Sulfanomide herbicides

ABSTRACT

A compound having the formula ##STR1## wherein A is CR 7  ; and R 1  through R 7  are substituents such as hydrogen, halogen, branched and straight chain hydrocarbons, cyclic hydrocarbons, aromatics, and sulfur and nitrogen containing functional groups. Further, R 5  and R 6  may be taken together with the atom to which they are attached to form a group ##STR2## in which R 9  and R 10  are further functional groups. The compounds are useful in herbicidal compositions, particularly in combination with carriers and surfactants. A process for making this compound is also presented.

FIELD OF THE INVENTION

The present invention relates to certain new sulfonamide derivatives,their preparation, herbicidal compositions containing them and their usein combating undesired plant growth.

BACKGROUND OF THE INVENTION

Sulfonamide compounds are well known for their biological activity.Certain classes of sulfonamide derivatives are useful as herbicideswhile other classes are useful as anti-bacterial agents.

In EP-A-0411706 it is disclosed that sulfonamide compounds of thegeneral formula ##STR3## in which A is a nitrogen atom or a group CR⁵,each of R¹, R², R³, and R⁵ is one of a range of moieties, and R⁴ is anoptionally substituted alkyl, aralkyl, aryl or heterocyclic group, orsalts thereof, exhibit herbicidal activity.

A class of sulfanomide derivatives has now been found which differstructurally from those disclosed in EP-A-0411706 in that the terminalgroup R⁴ has been replaced by a substituted amino group and which haveuseful herbicidal properties.

SUMMARY OF THE INVENTION

The present invention thus provides a compound of the general formula##STR4## in which A is a nitrogen atom or CR⁷ ;

R¹, R² and R⁷ each independently are hydrogen halogen formyl, cyano,carboxy or azido, or optionally substituted alkyl alkenyl, alkynyl,cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, aryloxy, alkylthio,alkenylthio, alkynylthio, arylthio, alkylcarbonyl, alkoxycarbonyl,amino, aminoxy, or dialkylaminoxy;

R³ is hydrogen, or optionally substituted alkyl, alkenyl, alkynyl,cycloalkyl, heterocyclic, aralkyl or aryl;

R⁴ is hydrogen, or optionally substituted alkyl, alkenyl, aralkyl, arylor heterocyclic group, or optionally substituted acyl group of theformula COR⁸ in which R⁸ is alkyl, aryl or aralkyl; and

R⁵ and R⁶ each independently are hydrogen, or optionally substitutedalkyl, alkoxy, alkenyl, akynyl, aryl, aralkyl, amino, cycloalkyl, orheterocyclic group, or a group of the formula --SO₂ R⁸, in which R⁸ isdefined above, or ##STR5## in which R¹¹ is an alkylthio group, or R⁵ andR⁶ together form a group ##STR6## in which R⁹ and R¹⁰ independently arehydrogen, or alkyl, alkoxy, aryl, aralkyl or dialkylamino, or R⁹ and R¹⁰together form an optionally substituted heterocyclic group, or R⁵ and R⁶together form an alkylene chain which is optionally interrupted by anoxygen, sulphur, or --NR-- in which R is hydrogen or alkyl or a saltthereof.

Each alkyl, alkenyl, or alkynyl independently is a straight or branchedchain group. Preferably each alkyl has from 1 to 12 carbon atoms, morepreferably from 1 to 6 carbon atoms, and especially from 1 to 4 carbonatoms. Alkenyl or alkynyl groups have from 2 to 12 carbon atoms,preferably from 2 to 6 carbon atoms and especially from 2 to 4 carbonatoms. Cycloalkyl groups have from 3 to 8 carbon atom ring members.

Each aryl is a single fused or carbocyclic ring system having from 6 to10 ring members. Preferably an aryl radical or moiety comprises a singlering system and preferably is a phenyl ring.

A heterocyclic radical is a single or fused, saturated or unsaturated,ring system having from 5 to 10 ring members preferably 5 or 6 ringmembers of which from 1 to 3 ring members are hetero atoms selected fromoxygen, nitrogen and sulphur atoms.

Radicals represented by the symbols R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰ are unsubstituted or substituted. Where substituents are present,the substituent groups are any of those customarily employed in themodification and/or development of pesticidal compounds and areespecially substituents that maintain or enhance the herbicidal activityassociated with the compounds of the present invention, or influencepersistence of action soil or plant penetration, or any other desirableproperty for herbicidal compounds. There may be one or more of the sameor different substituents present in each radical.

Substituents for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy, alkylthio, alkenylthio, alkylcarbonyl and alkoxycarbonyl oralkyl moieties in aralkyl groups are independently selected fromhalogen, alkoxy, alkenyloxy, aryloxy, hydroxy, alkylthio, arylthio,aryl, alkylsulfonyl, alkylsulfinyl, alkylenedioxy, alkylenedithio,haloalkyl, and alkoxycarbonyl groups, heterocyclic groups,dialkyliminoxy, optionally substituted amino, trialkylsilyl,alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, carboxy, cyano,thiocyanato, or optionally substituted aminocarbonyl groups.

Substituents for aryl, cycloalkyl aryloxy or arylthio groups,heterocyclic rings or aryl moieties in aralkyl groups are independentlyselected from halogen, nitro, cyano, alkyl, haloalkyl alkoxy,haloalkoxy, alkylthio, alkylsufonyl, mono- or di-alkylsulfonamido,aryloxy, carboxy, alkoxycarbonyl or aralkoxycarbonyl groups.

Substituents for amino groups are independently selected from alkyl,alkenyl, aryl, alkoxy, amino, mono- or di-alkylamino, arylamino,alkoxyalkyl, haloalkyl, hydroxy, hydroxyalkyl, cyano, carboxyalkyl oralkylcarbonylamino, or the amino group may form part of a heterocyclicring.

Suitable salts of the invention are agrochemically acceptable salts ofcompounds of general formula I. Salts are formed with inorganic ororganic cations by conventional methods. Such salts suitably includesalts with inorganic cations derived from alkali metals and alkalineearth metals such as, for example, sodium, potassium, calcium andmagnesium, and from transition metals, for example copper, or salts withorganic cations such as alkylammonium and alkylsulfonium cations.

A haloalkyl has from 1 to 3 halogen atoms. Halogen as a substituent issuitably fluorine, chlorine or bromine. A preferred haloalkyl radical istrifluoroethyl.

A is preferably nitrogen or CH.

Suitable examples of the radical R¹ include C₁₋₄ alkyl, C₁₋₄ alkoxy, andC₁₋₄ haloalkyl, preferably methyl, methoxy and trifluoromethyl groups.Suitable examples of the radical R² include C₁₋₄ alkyl, C₁₋₄ alkoxy andhalogen, preferably methyl, methoxy or chlorine.

Suitable examples of the radical R³ include C₁₋₆ alkyl and phenyl.Preferably the radical R³ is selected from methyl, ethyl, n-propyl,n-butyl, i-butyl, s-butyl, t-butyl or phenyl.

Preferably, R⁴ is hydrogen.

Suitably, R⁵ and R⁶ independently are hydrogen, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy, C₂₋₆ alkenyl, C₂₋₆ alkynyl, mono- or di-(C₁₋₆alkoxy)C₁₋₄ alkyl, (C₁₋₄ alkoxy) carbonyl (C₁₋₄ alkyl), C₃₋₈ cycloalkylor benzyl, or optionally substituted phenyl, pyridyl, pyrimidinyl, or(C₃₋₈ cycloalkyl)C₁₋₄ alkyl, or a group ##STR7## in which R¹¹ is a C₁₋₄alkylthio or R⁵ and R⁶ together form a group ##STR8## in which R⁹ andR¹⁰ independently are C₁₋₄ alkyl, C₁₋₄ alkoxy or di(C₁₋₄ alkyl)amino orand R⁹ and R¹⁰ together form a five-membered ring in which two or threering members are hetero atoms selected from nitrogen or sulphur atoms,the ring being substituted by a benzyl or one or two C₁₋₄ alkyl groups,or R⁵ and R⁶ together form an alkylene chain which is optionallyinterrupted by oxygen or --NR-- in which R is C₁₋₄ alkyl.

Preferably R⁵ is hydrogen or methyl or ethyl, R⁶ is hydrogen, methyl,ethyl, n-propyl, i-propyl, n-butyl, methoxy, chloroethyl,methoxycarbonylmethyl, mono- or di- methoxyethyl, allyl, propynyl,cyclopropyl, cyclobutyl, pyridyl, dimethylprimidinyl,(dichlorocyclopropyl)methyl, phenyl, chlorophenyl, benzyl or the group##STR9## or R⁵ and R⁶ together represent one of the groups ##STR10##together are --(CH₂)₂ O(CH₂)₂ --, --(CH₂)₂ N(CH₃)(CH₂)₂ -- or --(CH₂)₄--.

It will be appreciated that the compounds of the present invention inwhich R³ is other than a hydrogen atom have an asymmetric carbon atomand will therefore exist in different stereoisomeric forms. The presentinvention accordingly includes all individual isomeric forms of thecompounds of general formula I and mixtures thereof in whateverproportion. Thus, the R- and S-enantiomers of the compound of generalformula IA ##STR11## in which A, R¹, R², R⁴, R⁵ and R⁶ are ashereinbefore defined and R³ is other than hydrogen, and mixturesthereof, are included within the present invention.

In accordance with the present invention there is also provided aprocess for the preparation of a compound of the general formula I,which process comprises

(a) reacting a compound of the general formula II ##STR12## in which A,R¹, R², R³ are as defined above, or the corresponding ester, acidchloride or acid anhydride, with a compound of the general formula##STR13## in which R⁴, R⁵ and R⁶ are as previously defined or a saltthereof or, in an alternate embodiment,

(b) reacting a compound of the general formula ##STR14## in which A, R¹and R² are as previously defined and L¹ represents a leaving group, witha di-salt when R⁴ is hydrogen, and a mono-salt when R⁴ represents amoiety other than hydrogen, of the compound of the general formula##STR15## in which R³, R⁴, R⁵ and R⁶ are as previously defined.

The leaving group is any group that will, under the reaction conditions,cleave from the starting material thus promoting reaction at a specifiedsite. The leaving group L¹ is suitably halogen, for example, bromine,chlorine or iodine, or alkanesulfonyl, for example, methanesulfonyl.

The salt of compound V is suitably an alkali metal salt, preferably asodium salt.

Process (a) is suitably carried out at ambient or elevated temperature,i.e., at a temperature above 20° C. A preferred temperature range inwhich to carry out the reaction is from about 20° C. to about 80° C. Anespecially suitable reaction temperature is from about 20° C. to about50° C. The molar ratio of reactant II to reactant III is from about 1.0to about 5.0, preferably about from 1.0 to about 2.5.

The reaction (a) is carried out in an inert organic solvent such as ahydrocarbon covalent, e.g., benzene or toluene, a chlorinatedhydrocarbon, e.g., dichloromethane or chloroform, an alcohol, e.g.,methanol or ethanol, an ether, e.g., diethyl ether, tetrahydrofuran,1,4-dioxane, a ketone, e.g., acetone or methyl ethyl ketone, an estere.g., ethyl acetate, an aprotic polar solvent, e.g., dimethylformamide,dimethylacetamide or dimethylsulfoxide or a nitrile, e.g., acetonitrile.

Preferably, the reaction (a) is carried out in the presence of atertiary amine, for example, 1,8-diazabicyclo[5.4.0]undec-7-ene. Othersuitable tertiary amines include triethylamine and pyridine.

When the reactant II is in the form of a free carboxylic acid, thecarboxy group is preferably activated for the reaction to proceed by thepresence of a carbonyl-activating agent. Suitable carboxyl-activatingagents include 2-chloro-N-methyl pyridinium iodide,dicyclohexylcarbodiimide and carbonyldiimidazole. Suitably the acidreactant II is activated by the carboxyl-activating agent in thepresence of an inert organic solvent at ambient or elevated temperaturefrom about 20° C. to the reflux temperature of the mixture, prior to theaddition of reactant III, and if desired, the tertiary amine.

Process (b) is suitably carried out at a temperature from about ambientto the reflux temperature of the reaction medium, preferably from about100° C. to about 150° C., for example at 120° C. The molar ratio of thereactants IV:V is suitably from about 1.0 to about 2.5.

In reaction (b) the salt is suitably prepared from a compound V by theaction of an alkali metal, such as metallic sodium or potassium, orconveniently, a strong base, for example, an alkali metal hydride, suchas sodium or potassium hydride, an alkaline earth metal hydride, such ascalcium hydride, an alkali metal alkoxide, such as sodium or potassiumhydroxide. Suitably conversion of a hydroxy compound V to the saltoccurs in situ.

The reaction (b) is carried out in the presence of a solvent. Typicalsolvents are the same as those solvents noted above for process (a).

The compound of general formula I is converted to other compounds ofgeneral formula I by methods known to the art, provided that suitablecare is taken to ensure that the sulfonamide group is not affected. Thusfor example, a compound of general formula I where R¹ and/or R²represents a halogen atom, particularly chlorine, is transformed intoother derivatives by nucleophilic displacement, for example by reactionwith two equivalents of an amine, such as dimethylamine, to give thecorresponding compound of general formula I in which R¹ and/or R²represents a substituted amino group. Likewise a compound of generalformula I in which R¹ and/or R² represents a halogen atom, is reactedwith two equivalents of alkylthio organo-metallic compound, for examplesodium methanethiolate, to yield the corresponding compound of generalformula I in which R¹ and/or R² is a hydrogen atoms. Furthermore, acompound of general formula I in which R⁴ represents hydrogen isconverted by known methods into the corresponding compound of formula Iin which R⁴ represents a moiety other than a hydrogen atom.

Individual enantiomers are obtained using stereospecific reactants or byconventional resolution techniques.

The prepared compounds of the invention are, if desired, isolated andpurified using conventional techniques.

Suitable starting carboxylic acids of general formula II, and estersthereof, and also their preparation, are described and claimed inEP-A-0400741. Thus, the starting carboxylic acids of general formula II,and esters thereof, are prepared either by reacting a compound of thegeneral formula ##STR16## in which R¹, R² and A are defined above and Lis a leaving group, for example, a halogen atom or alkanesulfonyl group,with a compound of the general formula ##STR17## in which R³ is asdefined above, or an ester thereof, or for compounds in which Arepresents CR⁷, reacting a compound of the general formula ##STR18## inwhich R¹, R² and R⁷ are as defined above with an ester of a compound ofthe general formula ##STR19## in which R³ is as defined above and X is aleaving group such as a halogen atom or a sulfonyloxy group. The acidchloride and acid anhydride derivatives are prepared from the compoundsof formula II by standard techniques.

The reactants of general formula III are either known or are preparedusing techniques described in the literature. For example, the compoundsare prepared by methods such as those described in (A) G. Lohaus, Chem,Ber., 105, 2791 (1972) or in (B) G. Weiss and G. Schulze, Liebigs Ann.Chem., 729, 40 (1969).

The starting triazine compounds of general formulae IV and VI (i.e., inwhich A is nitrogen atom) are either known or are prepared usingtechniques described in the literature. For example, such compounds areprepared from 2,4,6-trichlorotriazine, by methods such as thosedescribed by Dudley et al, J. Am. Chem. Soc., 73, 2986 (1951); Koopmanet al, Rec. Trav. Chim., 79, 83 (1960); Hirt et al, Helv. Chim. Acta,33, 1365 (1950); Kobe et al, Monatshefte fur Chemie, 101, 724 (1970) andRoss et al, U.S. Pat. Specification No. 3,316,263.

The starting pyrimidines of general formulae IV, VI and VIII (i.e., inwhich A is a group CH) are prepared by conventional techniques, forexample those described in Heterocyclic compounds, 16, "ThePyrimidines", edited by D. J. Brown, Interscience, 1962.

The compounds of general formula V are prepared from the correspondingbenzyloxy derivatives ##STR20## by hydrogenation using gaseous hydrogenin conjunction with a palladium- or platinum-carbon catalyst. Thebenzyloxy derivatives are prepared in analogous fashion for reaction (a)above by the reaction of an appropriate 2-benzyloxycarboxylic acid##STR21## or reactive derivative thereof, with a compound of generalformula III described above, or a salt thereof.

The compounds of general formula VII are either known compounds or areprepared by conventional procedures. Compounds in which R³ represents anaryl group are prepared by treating the corresponding aldehyde, R³ CHO,with a suitable cyanide compound, for example, potassium cyanide ortrimethylsilylcyanide, with, respectively, zinc iodide or sodiumbisulfite, followed by conversion of the cyano substituent to the acidgroup. See, for example, Schnur and Morville, J. Med. Chem. 29, 770(1986) and U.S. Pat. Specification No. 4,537,623. Compounds in which R³represents an alkyl group are, for example, prepared by the method ofKolasa and Miller, J. Org. Chem 52, 4978 (1987), starting from asuitable amino acid with a two stage conversion.

The compounds of general formula I have been found to have usefulherbicidal activity. Accordingly, the present invention further providesa herbicidal composition comprising a compound of formula I as definedabove in association with at least one carrier.

A carrier in a composition according to the invention is any materialwith which the active ingredient is formulated to facilitate applicationto the locus to be treated, which is for example, a plant, seed or soil,or to facilitate storage, transport or handling. A carrier is usefully asolid or a liquid, including a material which is normally gaseous butwhich has been compressed to form a liquid, and any of the carriersnormally used in formulation herbicidal compositions may be used.Preferably compositions according to the invention contain 0.5% to 95%by weight of active ingredient.

Suitable solid carriers include natural and synthetic clays andsilicates, for example, natural silicas such as diatomaceous earths;magnesium silicates, for example, talcs; magnesium aluminum silicates,for example, attapulgites and vermiculites; aluminum silicates, forexample kaolinites, montmorillonites and micas; calcium carbonate;calcium sulfate; ammonium sulfate; synthetic hydrated silicon oxides andsynthetic calcium or aluminum silicates; elements, for example, carbonand sulfur; natural and synthetic resins, for example, coumarone resins,polyvinyl chloride, and styrene polymers and copolymers; solidpolychlorophenols; bitumen; waxes; and solid fertilizers, for example,superphosphates.

Suitable liquid carriers include water; alcohols, for example,isopropanol and glycols; ketones, for example, acetone, methyl ethylketone, methyl isobutylketone and cyclohexanone; ethers; aromatic oraraliphatic hydrocarbons, for example, benzene toluene and xylene;petroleum fractions, for example, kerosine and light mineral oils;chlorinated hydrocarbons, for example, carbon tetrachloride,perchloroethylene and trichloroethane. Mixtures of different liquids areoften suitable.

Agricultural compositions are often formulated and transported in aconcentrated form which is subsequently diluted by the user beforeapplication. The present of small amounts of a carrier which is also asurface active agent facilitates this process of dilution. Thuspreferably at least one carrier in a composition according to theinvention is a surface-active agent. For example, the compositionusefully contains at least two carriers, at least one of which is asurface-active agent.

A surface-active agent is an emulsifying agent, a dispersing agent orwetting agent. It is nonionic or ionic. Examples of suitablesurface-active agents include the sodium or calcium salts of polyacrylicacids and lignin sulfonic acids; The condensation of fatty acids oraliphatic amines or amides containing at least 12 carbon atoms in themolecule with ethylene oxide and/or propylene oxide; fatty acid estersof glycerol, sorbitan, sucrose or pentaerythritol; condensates of thesewith ethylene oxide and/or propylene oxide; condensation products offatty alcohol or alkyl phenols, for example p-octylphenol orp-octylcresol, with ethylene oxide and/or propylene oxide; sulfates orsulfonates of these condensation products; alkali or alkaline earthmetal salts, preferably sodium salts, of sulfuric or sulfonic acidesters containing at least 10 carbon atoms in the molecule, for examplesodium lauryl sulfate, sodium secondary alkyl sulfates, sodium salts ofsulfonated castor oil, and sodium alkylaryl sulfonates such asdodecylbenzene sulfonate; and polymers of ethylene oxide and copolymersof ethylene oxide and propylene oxide.

The compositions of the invention are formulated as wettable powders,dusts, granules, solutions, emulsifiable concentrates, emulsions,suspension concentrates and aerosols. Wettable powders usually contain25%, 50% or 75% wt of active ingredient and usually contain in additionto solid inert carrier, 3%-10% wt of a dispersing agent and, wherenecessary, 0-10% wt of stabilizer(s) and/or other additives such aspenetrants. Dusts are usually formulated as a dust concentrate having asimilar composition to that of a wettable powder but without adispersant, and are diluted in the field with further solid carrier togive a composition usually containing 0.5%-10% wt of active ingredient.Granules are usually prepared to have a size between 10 BS mesh and 100BS mesh (1.676 mm-0.152 mm), and are manufactured by agglomeration orimpregnation techniques. Generally, granules will contain 0.5%-75% wtactive ingredient and 0-10% wt of additives such as stabilizerssurfactants, slow release modifiers and binding agents. The so-called"dryflowable powders" consist of relatively small granules having arelatively high concentration of active ingredient. Emulsifiableconcentrates usually contain, in addition to a solvent and, whennecessary, co-solvent, 10%-50% wt/v active ingredient, 2%-20% wt/vemulsifiers and 0-20% wt/v of other additives such as stabilizers,penetrants and corrosion inhibitors. Suspension concentrates are usuallycompounded so as to obtain a stable, non-sedimenting flowable productand usually contain 10%-75% wt active ingredient, 0.5%-15% wt ofdispersing agents, 0.1%-10% wt of suspending agents such as protectingcolloids and thixotropic agents, 0-10% wt of other additives such asdefoamers, corrosion inhibitors, stabilizers and penetrants, and wateror an organic liquid in which the active ingredient is substantiallyinsoluble. Certain organic solids or inorganic salts are presentdissolved in the formulation to assist in preventing sedimentation or asanti-freeze agents for water.

Aqueous dispersions and emulsions, for example, compositions obtained bydiluting a wettable powder or a concentrate according to the inventionwith water, also are within the scope of the invention. The saidemulsions are of the water-in-oil or of the oil-in-water type, and havea thick `mayonnaise`-like consistency.

The composition of the invention may also contain other activeingredients, for example, compounds possessing insecticidal orfungicidal properties or other herbicides.

The present invention still further provides the use as a herbicide of acompound of the general formula I as defined above or a composition asdefined above and a method of combating undesired plant growth at alocus with such a compound or composition according to the presentinvention. The locus may, for example, be the soil or plants in a croparea. The dosage of active ingredient used is from 0.01 kg/ha to 10kg/ha, suitably 0.05 kg/ha to 4 kg/ha.

Examples 1-166 below illustrate the process of the present invention.Examples 1 and 2 illustrate the preparation of intermediates of generalformula III, by Methods (a) and (b) respectively, while Examples 3 to166 illustrate compounds of general formula I.

EXAMPLE 1

Preparation of 1-n-butylsulfamide

(i) A solution of chlorosulfonylisocyanate (60.9 g, 0.43 mol) in toluene(20 ml) was added dropwise to a stirred solution of2,4,5-trichlorophenol (84.9 g, 0.43 mol) in toluene (80 ml), whilemaintaining the temperature of the reaction mixture at or below 35° C.After the addition was complete, the mixture was refluxed for 3 hours,during which time copious amounts of hydrogen chloride were evolved. Themixture was then cooled to 40° C. and water was added dropwise until nofurther carbon dioxide was evolved. The white precipitate which formedwas collected by filtration and dried to give the crudeO-(2,4,5-trichlorophenyl)-sulfamate as white crystals (93.0 g, 78%),m.p. 153°-155° C., which was used without further purification.

(ii) O-(2,4,5-trichlorophenyl)-sulfamate (13.83 g, 50 mmol) was added intwo portions to a stirred solution of n-butylamine (4.94 ml, 50 mmol)and triethylamine (6.9 ml, 50 mmol) in acetonitrile (50 ml). Afterstirring for 5 min, the solution was evaporated in vacuo. The residuewas dissolved in ethyl acetate (50 ml) and the organic phase was washedwith 0.05N hydrochloric acid (2×25 ml). The organic phase was then dried(sodium sulfate) and evaporated in vacuo. The residue was purified byflash chromatography (ethyl acetate/petroleum ether, 40:60, followed bypure ethyl acetate) to give the 1-n-butylsulfamide as a pale brown waxysolid (2.52 g, 33%).

EXAMPLE 2

Preparation of 1-methylsulfamide

(i) Sulfuryl chloride (81.3 ml, 1.0 mol) and antimony V chloride (0.21ml, 1.7 mol) were added sequentially to a stirred suspension ofmethylamine hydrochloride (67.0 g, 1.0 mol) in acetonitrile (500 ml).The mixture was refluxed for 4 hours, during which time chlorine andhydrogen chloride gases were evolved. Further sulfuryl chloride (81.3ml, 1.0 mol) was added to the mixture, which was then refluxed again for4 hours. A final portion of sulfuryl chloride (40.7 ml, 0.5 mol) wasthen added and the mixture was refluxed overnight. The mixture was thencooled to room temperature and the solvent evaporated in vacuo. Theresidue was distilled (b.p. 55°-57° C./0.02 mBar) to givemethylsulfamoyl chloride as a colorless viscous oil (112 g, 86%).

(ii) Methylsulfamoyl chloride (10.0 g, 77 mmol) was added dropwiseslowly to a stirred solution of liquid ammonia (ca. 50 ml, excess) intetrahydrofuran (250 ml) at -40° C. A white precipitate was formed. Themixture was allowed to attain room temperature and the excess ammoniaand solvent were evaporated in vacuo. The white crystalline residue wasrecrystallized from ethyl acetate/hexane to give the title compound aswhite needles (5.53 g, 65%), m.p. 62°-65° C.

EXAMPLE 3

Preparation of1-[2-(4,6-dimethoxypyrimidin-2-yl)oxy-3,3-dimethylbutan-1-oyl]-3-methylsulfamide

A solution 2-(4,6-dimethoxypyrimidin-2-yl-oxy-3,3-dimethylbutan-1-oicacid (1.35 g, 5.0 mmol) in tetrahydrofuran (20 ml) was added dropwise toa stirred solution of carbonyldiimidazole (0.89 g, 5.5 mmol) intetrahydrofuran (40 ml) at room temperature. The mixture was heated toreflux for 30 min, then allowed to cool again to room temperature.N-methylsulfamide (0.55 g, 5.0 mmol) was added. After stirring themixture for 15 min, a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene(0.76 g, 5.0 mmol) in tetrahydrofuran (10 ml) was added to the residue.The mixture was then acidified with 5N hydrochloric acid until there wasno further precipitation. The mixture was extracted with ethyl acetate(4×25 ml) and the combined organic phases were dried (sodium sulfate)and evaporated in vacuo. The residue was purified by flashchromatography (dichloromethane/methanol, 97:3) to give the titlecompound as white crystals (0.97 g, 54%), m.p. 200°-202° C.

EXAMPLES 4 TO 166

By methods analogous to that of Example 3, further compounds of thegeneral formula I were prepared by reaction of compounds of generalformula II with compounds of general formula III. Details are given inTables I and II.

                                      TABLE I                                     __________________________________________________________________________     ##STR22##                                                                    Ex No                                                                             R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                            R.sup.5                                                                          R.sup.6    mp (°C.)                                                                    Yield (%)                                 __________________________________________________________________________    4   OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   164  36                                        5   OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  C.sub.6 H.sub.5                                                                          198  69                                        6   OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                           58  39                                        7   OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                    ##STR23##    225-227                                                                            19                                        8   OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   (CH.sub.2).sub.4                                                                            145- 147                                                                           55                                        9   OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         C.sub.6 H.sub.5                                                                          134-136                                                                            40                                        10  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  nC.sub.4 H.sub.9                                                                         164-167                                                                            49                                        11  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.5                                                                 170-171                                                                            60                                        12  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   115-120                                                                            76                                        13  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   118-120                                                                            60                                        14  CH.sub.3                                                                          CH.sub.3                                                                          iC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   133-136                                                                            74                                        15  CH.sub.3                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5                                                                    CH.sub.3                                                                         CH.sub.3   187  36                                        16  OCH.sub.3                                                                         OCH.sub.3                                                                         C.sub.6 H.sub.5                                                                    H  C.sub.6 H.sub.5                                                                          192-193                                                                            55                                        17  OCH.sub.3                                                                         OCH.sub.3                                                                         C.sub.6 H.sub.5                                                                    CH.sub.3                                                                         C.sub.6 H.sub.5                                                                          137-138                                                                            55                                        18  OCH.sub.3                                                                         Cl  iC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   150-152                                                                            41                                        19  OCH.sub.3                                                                         Cl  iC.sub.4 H.sub.9                                                                   H  CH.sub.3   166-168                                                                            24                                        20  CH.sub.3                                                                          CH.sub.3                                                                          nC.sub.4 H.sub.9                                                                   H  CH.sub.3   154-156                                                                            42                                        21  OCH.sub.3                                                                         CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   123-124                                                                            56                                        22  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H                                                                                 ##STR24## 188-189                                                                            73                                        23  CH.sub.3                                                                          CH.sub.3                                                                          sC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   150  60                                        24  CH.sub.3                                                                          CH.sub.3                                                                          sC.sub.4 H.sub.9                                                                   H  CH.sub.3   161  72                                        25  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   CH.sub.3                                                                         CH.sub.3   123-126                                                                            30                                        26  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   H  CH.sub.3   166-169                                                                            73                                        27  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  CH.sub.3   178-180                                                                            76                                        28  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H                                                                                 ##STR25## 185-186                                                                            79                                        29  OCH.sub.3                                                                         CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  CH.sub.3   188-189                                                                            76                                        30  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  CH.sub.2 CF.sub.3                                                                        159-161                                                                            54                                        31  OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  CH.sub.3   150-153                                                                            79                                        32  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  nC.sub.3 H.sub.7                                                                         159-160                                                                            60                                        33  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  iC.sub.3 H.sub.7                                                                         172-173                                                                            58                                        34  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  nC.sub.4 H.sub.9                                                                         175-176                                                                            66                                        35  OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   122-123                                                                            53                                        36  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H                                                                                 ##STR26## 155-158                                                                            52                                        37  OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                   H  CH.sub.3   171-174                                                                            79                                        38  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                    ##STR27##    236-238                                                                            79                                        39  OCH.sub.3                                                                         CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H                                                                                 ##STR28## 190-192                                                                            59                                        40  CH.sub.3                                                                          CH.sub.3                                                                          nC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   123-124                                                                            50                                        41  OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         CH.sub.3   75-77                                                                              21                                        42  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                                                                      136-139                                                                            70                                        43  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  CH.sub.2 CCH                                                                             155-156                                                                            66                                        44  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  (CH.sub.2).sub.4                                                                         115-118                                                                            42                                        45  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                   H  CH.sub.3   156-159                                                                            63                                        46  CH.sub.3                                                                          CH.sub.3                                                                          iC.sub.4 H.sub.9                                                                   H  CH.sub.3   174-176                                                                            73                                        47  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                   H  nC.sub.4 H.sub.9                                                                         133-135                                                                            59                                        48  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                          154-156                                                                            76                                        49  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                                                                          173-175                                                                            68                                        50  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                                                                          176-178                                                                            65                                        51  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   H  C.sub.2 H.sub.5                                                                          177-178                                                                            72                                        52  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                                                                          147-149                                                                            74                                        53  CH.sub.3                                                                          CH.sub.3                                                                          iC.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                                                                          169-171                                                                            73                                        54  OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                                                                          142-144                                                                            77                                        55  CH.sub.3                                                                          CH.sub.3                                                                          nC.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                                                                          107-108                                                                            53                                        56  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  nC.sub.3 H.sub.7                                                                         170-171                                                                            73                                        57  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  iC.sub.3 H.sub.7                                                                         191-192                                                                            54                                        58  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   H  nC.sub.3 H.sub.7                                                                         165-167                                                                            74                                        59  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   H  iC.sub.3 H.sub.7                                                                         179-182                                                                            57                                        60  CH.sub.3                                                                          CH.sub.3                                                                          nC.sub.3 H.sub.7                                                                   H  CH.sub.3   151-154                                                                            58                                        61  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                    ##STR29##    110-113                                                                            33                                        62  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H   H         176  63                                        63  OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.3 H.sub.7                                                                   H  CH.sub.3   177-179                                                                            70                                        64  CH.sub.3                                                                          CH.sub.3                                                                          nC.sub.3 H.sub.7                                                                   H  CH.sub.3   151-154                                                                            58                                        65  OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.3 H.sub.7                                                                   CH.sub.3                                                                         CH.sub.3   74-76                                                                              35                                        66  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         C.sub.2 H.sub.5                                                                          131-134                                                                            48                                        67  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         C.sub.2 H.sub.5                                                                          120-122                                                                            47                                        68  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                                                                      169-171                                                                            71                                        69  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  CH.sub.2 CCH                                                                             155-156                                                                            51                                        70  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   H  CH.sub.2 CCH                                                                             165-168                                                                            80                                        71  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  CH.sub.2 CO.sub.2 CH.sub.3                                                               148-151                                                                            61                                        72  OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  CH.sub.2 CCH                                                                             130- 134                                                                           67                                        73  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         OCH.sub.3  112-115                                                                            11                                        74  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                   H  CH.sub.2 CCH                                                                             154-157                                                                            74                                        75  OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                                                                      131-134                                                                            69                                        76  OCH.sub.3                                                                         OCH.sub.3                                                                         C.sub.6 H.sub.5                                                                    H  CH.sub.3   191-193                                                                            69                                        77  OCH.sub.3                                                                         OCH.sub.3                                                                         C.sub.6 H.sub.5                                                                    CH.sub.3                                                                         CH.sub.3   148-151                                                                            54                                        78  OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                   H  CH.sub.2 CCH                                                                             145-148                                                                            18                                        79  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  H          178-181                                                                            39                                        80  OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  H          161-163                                                                            94                                        81  OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                   H  H          157  34                                        82  OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.3 H.sub.7                                                                   H  H          156-157                                                                            43                                        83  CH.sub.3                                                                          CH.sub.3                                                                          iC.sub.4 H.sub.9                                                                   H  H          162-163                                                                            63                                        84  OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         C.sub. 2 H.sub.5                                                                         oil  76                                        85  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  (CH.sub.2).sub.2 Cl                                                                      169-171                                                                            64                                        86  CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                   H  (CH.sub.2).sub.2 Cl                                                                      158-161                                                                            63                                        87  CH.sub.3                                                                          CH.sub.3                                                                          nC.sub.4 H.sub.9                                                                   H  CH.sub.2 CCH                                                                             106-109                                                                            32                                        88  OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                                                                      152-154                                                                            15                                        89  CH.sub.3                                                                          CH.sub.3                                                                          iC.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                                                                      123-126                                                                            34                                        90  CH.sub.3                                                                          CH.sub.3                                                                          nC.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                                                                      119-123                                                                            46                                        91  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  CH.sub.2 CH(OCH.sub.3).sub.2                                                             149-152                                                                            72                                        92  CF.sub.3                                                                          OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  H          93-96                                                                              24                                        93  CF.sub.3                                                                          OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  CH.sub.3   179-181                                                                            29                                        94  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H                                                                                 ##STR30## 158-161                                                                            32                                        95  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub. 4 H.sub.9                                                                  CH.sub.3                                                                         CH.sub.2 C.sub.6 H.sub.5                                                                 oil  29                                        96  OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H                                                                                 ##STR31## 156  13                                        97  OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.3 H.sub.7                                                                   H  CH.sub.2 CHCH.sub.2                                                                      154-156                                                                            75                                        98  OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.3 H.sub.7                                                                   H  CH.sub.2 CCH                                                                             159-161                                                                            67                                        99  CH.sub.3                                                                          CH.sub.3                                                                          iC.sub.4 H.sub.9                                                                   H  CH.sub.2 CCH                                                                             139-141                                                                            67                                        100 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.3 H.sub.7                                                                   H                                                                                 ##STR32## 183-186                                                                            43                                        101 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                                                                      138-140                                                                            45                                        102 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                   H                                                                                 ##STR33## 175-177                                                                            52                                        103 CH.sub.3                                                                          CH.sub.3                                                                          iC.sub.4 H.sub.9                                                                   H                                                                                 ##STR34## 160-164                                                                            58                                        104 OCH.sub.3                                                                         OCH.sub. 3                                                                        nC.sub.4 H.sub.9                                                                   H                                                                                 ##STR35## 178-182                                                                            37                                        105 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H                                                                                 ##STR36## 167-169                                                                            54                                        106 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.3 H.sub.7                                                                   H  C.sub.2 H.sub.5                                                                          160-164                                                                            56                                        107 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.3 H.sub.7                                                                   H  nC.sub.3 H.sub.7                                                                         155-158                                                                            37                                        108 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                                                                          170-172                                                                            21                                        109 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  nC.sub.3 H.sub.7                                                                         93-97                                                                              16                                        110 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  OCH.sub.3  176-179                                                                            37                                        111 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   H  H          166-169                                                                            93                                        112 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   H                                                                                 ##STR37## 186-188                                                                            39                                        113 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   H  CH.sub.2 CHCH.sub.2                                                                      155-157                                                                            40                                        114 OCH.sub.3                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3   139-143                                                                            15                                        115 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                   H  H          169-170                                                                            52                                        116 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub. 4 H.sub.9                                                                  H  (CH.sub.2).sub.2 Cl                                                                      158-160                                                                            27                                        117 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                   H  (CH.sub.2).sub.2 Cl                                                                      174-175                                                                            53                                        118 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  (CH.sub.2).sub.2 Cl                                                                      147-150                                                                            43                                        119 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                   H  (CH.sub.2).sub.2 Cl                                                                      163-165                                                                            51                                        120 OCH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.3                                                                           H  nC.sub.4 H.sub.9                                                                         138-141                                                                            40                                        121 OCH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.3                                                                           H  CH.sub.2 C.sub.6 H.sub.5                                                                 183-184                                                                            47                                        122 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  nC.sub.4 H.sub.9                                                                         127-129                                                                            40                                        123 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  iC.sub.3 H.sub.7                                                                         156-157                                                                            11                                        124 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                   H  nC.sub.3 H.sub.7                                                                         154-155                                                                            31                                        125 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  (CH.sub.2).sub.2 OCH.sub.3                                                               132-135                                                                            68                                        126 OCH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.3                                                                           H                                                                                 ##STR38## 171-173                                                                            26                                        127 OCH.sub.3                                                                         OCH.sub.3                                                                         C.sub.6 H.sub.5                                                                    H  H          177-178                                                                            32                                        128 CH.sub.3                                                                          CH.sub.3                                                                          nC.sub.4 H.sub.9                                                                   H  H          169-170                                                                            25                                        129 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H                                                                                 ##STR39## 156-157                                                                            53                                        130 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         OCH.sub.3  138-144                                                                            10                                        131 OCH.sub.3                                                                         OCH.sub.3                                                                         C.sub.6 H.sub.5                                                                    H  CH.sub.2 C.sub.6 H.sub.5                                                                 200-201                                                                            41                                        132 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                   CH.sub.3                                                                         C.sub.2 H.sub.5                                                                          103-104                                                                             4                                        133 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                   H  OCH.sub.3  136-137                                                                            33                                        134 OCH.sub.3                                                                         OCH.sub.3                                                                         C.sub.2 H.sub.5                                                                    H  H          167-168                                                                            77                                        135 OCH.sub.3                                                                         OCH.sub.3                                                                         C.sub.2 H.sub.5                                                                    H  CH.sub.3   171-174                                                                            59                                        136 OCH.sub.3                                                                         OCH.sub.3                                                                         C.sub.2 H.sub.5                                                                    CH.sub.3                                                                         CH.sub.3   oil  55                                        137 CH.sub.3                                                                          OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   H  H          182-184                                                                            47                                        138 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   C.sub.2 H.sub.5                                                                  C.sub.2 H.sub.5                                                                          134-142                                                                            39                                        139 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                    ##STR40##    207-211                                                                            80                                        140 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                    ##STR41##    148-151                                                                            78                                        141 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                    ##STR42##    178-180                                                                            33                                        142 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 h.sub.7                                                                    ##STR43##    148-150                                                                            19                                        143 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.3 H.sub.7                                                                    ##STR44##    167-170                                                                            27                                        144 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                    ##STR45##    235-238                                                                            60                                        145 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                    ##STR46##    187-189                                                                            63                                        146 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                    ##STR47##    178-179                                                                            11                                        147 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                    ##STR48##    160-162                                                                            13                                        148 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.3 H.sub.7                                                                    ##STR49##    171-173                                                                            12                                        149 OCH.sub. 3                                                                        OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                    ##STR50##    187-191                                                                            54                                        150 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                    ##STR51##    172-176                                                                            58                                        151 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                    ##STR52##    183-185                                                                            11                                        152 CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                    ##STR53##    175-176                                                                            35                                        153 CH.sub.3                                                                          OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                    ##STR54##    181-184                                                                            55                                        154 OCH.sub.3                                                                         OCH.sub.3                                                                         sC.sub.4 H.sub.9                                                                    ##STR55##    111-112                                                                            38                                        155 OCH.sub.3                                                                         OCH.sub.3                                                                         iC.sub.4 H.sub.9                                                                    ##STR56##    126-128                                                                            39                                        156 OCH.sub.3                                                                         OCH.sub.3                                                                         nC.sub.4 H.sub.9                                                                    ##STR57##    129-130                                                                            41                                        157 CH.sub.3                                                                          CH.sub.3                                                                          tC.sub.4 H.sub.9                                                                    ##STR58##    151-153                                                                            22                                        158 CH.sub.3                                                                          OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                    ##STR59##    oil  28                                        __________________________________________________________________________

                                      TABLE II                                    __________________________________________________________________________     ##STR60##                                                                    Ex No                                                                             R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                           R.sup.5                                                                          R.sup.6                                                                              mp (°C.)                                                                    Yield (%)                                      __________________________________________________________________________    159 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                  H  H      145-148                                                                            62                                             160 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                  H  CH.sub.3                                                                             187-188                                                                            54                                             161 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                  CH.sub.3                                                                         CH.sub.3                                                                             oil  32                                             162 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                  CH.sub.3                                                                         C.sub.2 H.sub.5                                                                      oil  21                                             163 CH.sub.3                                                                          OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                  H  CH.sub.3                                                                             141-144                                                                            35                                             164 CH.sub.3                                                                          OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                  H  H      179-180                                                                            65                                             165 OCH.sub.3                                                                         OCH.sub. 3                                                                        tC.sub.4 H.sub.9                                                                   ##STR61##                                                                              oil  16                                             166 OCH.sub.3                                                                         OCH.sub.3                                                                         tC.sub.4 H.sub.9                                                                   ##STR62##                                                                              200-104                                                                            39                                             __________________________________________________________________________

Elemental analysis or n.m.r. data for the compounds of general formula Idescribed above is set out in Table III below.

                  TABLE II                                                        ______________________________________                                        .sup.1 H n.m.r. - chemical shift, δ, in p.p.m.                          for solutions in CDCl.sub.3 (unless otherwise indicated)                      or Analysis %                                                                 C               H            N                                                Ex No  Calc.   Found    Calc. Found  Calc. Found                              ______________________________________                                         3     43.1    43.3     6.1   6.2    15.5  15.5                                4     44.7    44.9     6.4   6.7    14.9  15.0                                5     50.9    51.2     5.7   6.0    13.2  13.1                                6     1.1(9H, s), 3.3(4H, m), 3.7(4H, m), 3.9(6H, s),                               4.9(1H, s), 5.7(1H, s), 8.4(1H, br.s)                                   7     47.3    47.4     6.8   6.9    16.2  16.0                                8     1.1(9H, s), 1.9(4H, m), 3.3-3.5(4H, m), 3.9(6H, s),                           4.9(1H, s), 5.8(1H, s), 8.5(1H, br.s)                                   9     52.0    52.1     6.0   6.2    12.8  12.8                               10     0.9(3H, t), 1.1(9H, s), 1.3(2H, m), 1.5(2H, m),                               2.9(2H, q), 3.9(6H, s), 4.9(1H, s), 5.1(1H, br.t),                            5.8(1H, s), 8.5(1H, br.s)                                              11     52.0    52.1     6.0   6.3    12.8  12.8                               12     44.7    44.4     6.4   6.6    14.9  14.6                               13     48.8    49.0     7.0   6.8    16.3  16.2                               14     48.8    48.9     7.0   7.0    16.3  16.1                               15     52.7    53.1     5.5   5.6    15.4  15.5                               16     54.0    54.3     4.5   4.5    12.6  12.6                               17     55.0    55.1     4.8   4.8    12.2  12.2                               18     41.0    41.1     5.6   5.6    14.7  14.6                               19     39.3    40.1     5.2   5.3    15.3  15.2                               20     47.3    47.7     6.7   6.8    17.0  17.1                               21     46.7    46.9     6.7   6.8    15.5  15.4                               22     46.4    46.4     6.2   6.2    14.4  14.4                               23     48.8    48.5     7.0   6.9    16.3  16.1                               24     47.3    47.3     6.7   6.6    17.0  16.8                               25     43.1    43.4     6.1   5.7    15.5  15.5                               26     41.4    41.3     5.8   5.9    16.1  16.1                               27     47.3    47.2     6.7   6.7    17.0  16.9                               28     50.5    50.7     6.8   6.7    15.7  15.8                               29     45.1    45.2     6.4   6.3    16.2  16.3                               30     39.1    39.2     4.9   5.0    13.0  12.9                               31     43.1    43.5     6.1   6.0    15.5  15.7                               32     46.1    46.1     6.7   6.7    14.3  14.5                               33     46.1    45.9     6.7   6.7    14.3  14.1                               34     51.6    51.6     7.6   7.3    15.0  15.1                               34     44.7    44.8     6.4   6.4    14.9  15.0                               36     1.1(9H, s), 1.5-2.3(6H, m), 3.7(1H, m), 3.9(6H, s),                           5.0(1H, s), 5.4(1H, d), 5.7(1H, s), 8.5(1H, br.s)                      37     43.1    43.1     6.1   6.1    15.5  15.2                               38     43.1    43.4     5.2   5.2    15.7  15.8                               39     48.4    48.2     6.5   6.4    15.0  14.9                               40     48.8    49.1     7.0   7.0    16.3  16.4                               41     0.8(3H, t), 1.0(3H, m), 1.2(1H, m), 1.5(1H, m),                               2.0(1H, m), 2.8(2x3H, s), 3.8(6H, s), 5.1 and                                 5.3(1H, 2xd), 5.7(1H, s), 8.5(1H, br.s)                                42     46.4    46.2     6.2   6.6    14.4  14.5                               43     46.6    46.0     5.7   5.9    14.5  14.4                               44     1.1(9H, s), 1.8(4H, m), 2.4(6H, s), 3.4(4H, m),                               5.0(1H, s), 6.7(1H, s), 8.4(1H, br.s)                                  45     43.1    42.8     6.1   6.1    15.5  15.8                               46     47.3    46.8     6.7   6.7    17.0  17.1                               47     47.5    47.4     7.0   7.0    13.9  14.2                               48     49.7    49.8     6.8   6.9    14.5  14.7                               49     44.7    44.5     6.4   6.5    14.9  15.1                               50     48.8    48.5     7.0   7.1    16.3  16.3                               51     43.1    42.6     6.1   6.2    15.5  15.6                               52     0.9(6H, dd), 1.1(3H, t), 1.7(1H, m), 1.8(2H, m),                              2.9(2H, q), 3.8(6H, s), 5.2(1H, br.t), 5.3(1H, dd),                           5.7(1H, s), 8.6(1H, br.s)                                              53     0.9(6H, dd), 1.1(3H, t), 1.7-1.9(2H, m), 2.4(6H, s),                          3.0(2H, m), 5.1(1H, br.t), 5.5(1H, dd), 6.7(1H, s),                           8.9(1H, br.s)                                                          54     1.0(3H, m), 1.1(3H, dd), 1.2(3H, dt), 1.2-1.6(2H, m),                         2.0(1H, m), 3.0(2H, m), 3.9(6H, s), 5.1(1H, br.m),                            5.2 and 5.4(1H, 2xd), 5.8(1H, s), 8.6(1H, br.s)                        55     48.8    48.4     7.0   7.0    16.3  16.4                               56     0.9(3H, t), 1.1(9H, s), 1.5(2H, m), 2.5(6H, s), 2.8(2H, q),                   5.1(1H, s), 5.2(1H, br.t), 6.7(1H, s), 8.5(1H, br.s)                   57     1.0(6H, dd), 1.1(9H, s), 2.4(6H, s), 3.4(1H, m),                              5.0(1H, br.d), 5.1(1H, s), 6.7(1H, s), 8.5(1H, br.s)                   58     0.9(3H, t), 1.1(6H, dd), 1.5(2H, m), 2.3(1H, m),                              2.9(2H, m), 3.9(6H, s), 5.1(1H, s), 5.2(1H, s), 5.7(1H, s),                   8.5(1H, br.s)                                                          59     1.1(6H, dd), 1.2(6H, dd), 2.8(1H, m), 3.5(1H, m),                             3.9(6H, s), 5.0(1H, br.d), 5.2(1H, d), 5.7(1H, s),                            8.6(1H, br.s)                                                          60     0.9(3H, t), 1.5(2H, m), 2.0(2H, m), 2.4(6H, s),                               2.7(3H, d), 5.3(1H, br.q), 5.4(1H, t), 6.7(1H, s),                            9.0(1H, br.s)                                                          61     1.1(9H, s), 1.2(3H, t), 2.5(3H, s), 3.9(6H, s), 4.1(2H, q),                   4.8(1H, s), 5.7(1H, s), 8.8(1H, br.s)                                  62     1.1(9H, s), 3.9(6H, s), 5.0(1H, s), 5.6(2H, br.s),                            5.7(1H, s), 9.0(1H, br.s)                                              63     1.0(3H, t), 1.5(2H, m), 2.0(2H, m), 2.7(3H, d),                               3.9(6H, s), 5.2(1H, br.q), 5.3(1H, t), 5.7(1H, s),                            8.7(1H, br.s)                                                          64     0.9(3H, t), 1.5(2H, m), 2.0(2H, m), 2.4(6H, s),                               2.6(3H, d), 5.4(1H, q), 5.5(1H, t), 6.8(1H, S),                               9.0(1H, br s)                                                          65     43.1    42.5     6.1   6.4    15.5  15.5                               66     46.1    46.3     6.7   6.8    14.3  14.7                               67     50.3    50.2     7.3   7.3    15.6  15.7                               68     1.1(9H, s), 1.7(1H, br s), 2.4(6H, s), 3.5(2H, m),                            5.2-5.0(3H, m), 5.7(1H, m), 6.8(1H, s), 8.6(1H, br s)                  69     1.1(9H, s), 1.7(1H, br s), 2.2(1H, t), 2.4(6H, s),                            3.8(2H, m), 5.5(1H, br s), 6.7(1H, s), 8.7(1H, br s)                   70     1.0(3H, d), 1.1(3H, d), 2.2(1H, t), 2.3(1H, m),                               3.8(2H, d), 3.9(6H, s), 5.2(1H, d), 5.7(1H, s)                         71     1.1(9H, s), 3.7(3H, s), 3.8(2H, s), 3.9(6H, s), 4.9(1H, s),                   5.7(1H, s)                                                             72     46.6    47.1     5.7   5.8    14.5  14.5                               73     1.1(9H, s), 1.6(1H, br s), 3.0(3H, s), 3.6(3H, s),                            3.9(9H, s), 4.9(1H, s), 5.7(1H, s)                                     74     46.6    47.0     5.7   6.1    14.5  14.7                               75     46.4    46.6     6.2   6.5    14.4  14.6                               76     47.1    47.3     4.7   5.0    14.7  14.9                               77     48.5    48.8     5.1   5.3    14.1  14.2                               78     0.9(3H, t), 1.3-1.6(4H, m), 1.9-2.1(2H, q), 2.2(1H, t),                       3.8(2H, br d), 3.9(6H, s), 5.3(1H, dd), 5.8(1H, s)                     79     45.6    45.4     6.4   6.6    17.7  17.7                               80     41.4    40.6     5.8   6.1    16.1  15.7                               81     41.4    41.8     5.8   6.2    16.1  16.4                               82     39.5    39.4     5.4   5.6    16.8  16.8                               83     45.6    45.8     6.4   6.7    17.7  17.5                               84     0.9(3H, q), 1.0-1.8(8H, m), 2.1(1H, m), 2.9(3H, 2xs),                         3.3(2H, m), 3.6(1H, m), 3.8(6H, s), 5.1 and                                   5.2(1H, 2 x d), 5.7(1H, s), 8.5(1H, br s)                              85     40.9    41.2     5.6   6.0    13.6  13.7                               86     44.4    44.0     6.1   6.4    14.8  14.8                               87     0.9(3H, t), 1.2-1.5(4H, m), 2.0(2H, br q), 2.2(1H, t),                        2.4(6H, s), 3.8(2H, br m), 5.4(1H, dd), 5.6(1H, br s),                        6.7(1H, s)                                                             88     46.4    46.3     6.2   6.4    14.4  14.5                               89     1.0(6H, dd), 1.6-2.0(3H, m), 2.4(6H, s), 3.5(2H, br s),                       5.1-5.4(4H, m), 5.7(1H, m), 6.8(1H, s)                                 90     50.6    49.9     6.8   7.0    15.7  15.8                               91     44.0    44.1     6.5   6.8    12.8  12.9                               92     37.3    38.0     4.4   4.8    14.5  14.6                               93     39.0    39.2     4.8   5.0    14.0  13.9                               94     48.0    47.5     5.4   5.6    16.5  17.2                               95     1.0(9H, s), 2.6(3H, s), 3.8(6H, s), 4.3(2H, s), 4.8(1H, s),                   5.7(1H, s), 8.7(1H, br s)                                              96     1.0(9H, s), 2.3(6H, s), 2.4(1H, s), 3.8(6H, s), 4.7(1H, s),                   5.5(1H, s), 6.4(1H, s)                                                 97     1.0(3H, t), 1.5(2H, m), 2.0(2H, m), 3.6(2H, br m),                            3.9(6H, s), 5.1-5.3(3H, m), 5.7(1H, m)                                 98     44.2    44.9     5.4   5.3    15.1  14.6                               99     1.0(6H, dd), 1.8-2.0(3H, m), 2.2(1H, t), 2.4(6H, s),                          3.8(2H, m), 5.5(1H, dd), 5.6(1H, m), 6.7(1H, s)                        100    44.9    44.6     5.9   6.1    15.0  14.7                               101    46.4    46.2     6.2   6.5    14.4  14.3                               102    46.4    46.1     6.2   6.3    14.4  14.5                               103    0.6(2H, m), 0.7(2H, m), 0.9(6H, dd), 1.7-2.0(2H, m),                          2.2(1H, m), 2.4(6H, s), 5.5(1H, dd), 5.7(1H, br s)                     104    0.7(2H, m), 0.8(2H, m), 0.9(3H, t), 1.3-1.6(4H, m),                           2.0(2H, q), 2.1(1H, br s), 2.3(1H, m), 3.9(6H, s),                            5.3(1H, t), 5.7(1H, s), 9.1(1H, br s)                                  105    46.4    46.8     6.2   6.4    14.4  14.8                               106    43.1    43.4     6.1   6.4    15.5  15.9                               107    44.7    44.8     6.4   6.7    14.9  15.0                               108    44.7    45.0     6.3   6.6    14.9  14.9                               109    0.8-0.9(6H, 2xm), 1.0(3H, 2xd), 1.3-1.7(4H, m),                               2.0(1H, m), 2.9(2H, q), 3.9(6H, s), 5.6(1H, m),                               5.7(1H, 2xd)                                                           110    1.0(9H, s), 1.8(1H, br s), 3.7(3H, s), 3.8(6H, s),                            4.9(1H, s), 5.7(1H, s), 8.0(1H, br s)                                  111    44.3    44.8     2.8   3.1    21.5  21.9                               112    44.9    44.3     5.9   5.9    14.7  15.0                               113    44.9    44.2     5.9   5.6    14.7  14.8                               114    1.6(3H, d), 2.9(6H, s), 3.9(6H, s), 5.3(1H, q), 5.7(1H, s),                   8.5(1H, br s)                                                          115    41.4    41.2     5.8   5.8    16.1  15.8                               116    40.9    41.1     5.6   5.8    13.6  13.6                               117    40.9    40.7     5.6   5.6    13.6  13.7                               118    40.9    40.7     5.6   5.7    13.6  13.7                               119    39.4    40.0     5.3   5.9    14.1  14.6                               120    43.0    42.6     6.1   6.8    15.5  16.1                               121    48.5    48.7     5.1   5.6    14.1  14.8                               122    47.5    48.0     7.0   7.6    13.9  14.7                               123    46.1    45.5     6.1   6.8    14.4  14.8                               124    46.1    45.8     6.7   6.7    14.4  15.0                               125    1.1(9H, s), 3.1(2H, br m), 3.3(3H, s), 3.4(2H, t),                            3.9(6H, s), 4.9(1H, s), 5.6(1H, br s), 5.7(1H, s)                      126    43.2    43.2     4.1   4.5    13.4  13.8                               127    45.7    45.2     4.4   4.8    15.2  15.3                               128    45.6    44.9     6.4   6.6    17.7  17.8                               129    1.0(9H, s), 1.2(1H, d t), 1.6(1H, d d), 1.9(1H m),                            3.0(1H, m), 3.3(1H, m), 3.9(6H, s), 4.9(1H, s),                               5.6(1H, br m), 5.7(1H, s), 8.6(1H, br s)                               130    0.8-1.0(6H, m), 1.2-1.7(2H, m), 2.0(1H, m), 2.6(3H, s),                       3.6(3H, s), 3.9(6H, s), 4.9(1H, 2xd), 5.7(1H, s)                              (in d.sup.6 -DMSO)                                                     131    1.8(1H, br s), 3.9(6H, s), 4.0(1H, m), 4.1(1H dd),                            5.5(1H, br t), 5.7(1H, s), 6.1(1H, s), 7.0-7.5(10H, m),                       9.2(1H, br s)                                                          132    46.1    45.8     6.7   6.9    14.4  14.4                               133    41.3    41.4     5.9   5.7    14.8  14.9                               134    37.5    37.2     5.0   5.6    17.5  17.4                               135    39.5    39.1     5.4   5.8    16.8  16.7                               136    1.0(3H, t), 2.0(2H, m), 2.8(6H, s), 3.3(6H, s), 5.0(1H, t),                   5.6(1H, s), 8.9(1H, br s)                                              137    43.1    42.5     6.1   6.4    15.5  15.5                               138    47.5    46.9     7.0   7.6    13.9  13.9                               139    41.7    42.3     5.3   5.7    18.2  17.7                               140    41.7    41.8     5.3   5.3    18.2  18.2                               141    1.1(9H, s), 1.7(1H, br s), 2.3(3H, s), 3.9(H, s),                             4.3(1H, s), 5.7(1H, s), 8.5(1H, br s)                                  142    44.6    45.2     6.0   6.4    13.9  14.1                               143    40.4    40.8     5.0   5.2    18.8  19.1                               144    44.4    44.3     5.5   5.7    15.2  15.2                               145    50.7    49.9     5.2   5.0    13.4  13.4                               146    41.8    41.1     5.3   5.0    18.3  18.0                               147    41.7    41.1     5.3   5.3    18.3  18.2                               148    40.4    40.7     5.0   5.2    18.8  18.4                               149    1.0(9H, s), 2.8(3H, s), 3.1(3H, s), 3.9(6H, s), 3.6(1H, s),                   5.8(1H, s), 8.0(1H, s), 11.6(1H, s)                                    150    50.3    50.2     7.3   7.3    15.6  15.7                               151    47.5    47.1     7.0   7.2    13.9  13.4                               152    46.5    45.6     5.6   6.1    16.9  16.7                               153    44.7    44.1     5.4   5.8    16.3  16.2                               154    45.9    45.4     6.3   6.8    13.4  13.6                               155    45.9    45.4     6.3   6.8    13.4  13.4                               156    45.9    45.5     6.3   6.7    13.4  13.4                               157    1.1(9H, s), 1.3(3H, t), 2.4(6H, s), 2.5(3H, s), 4.1(2H, q),                   5.1(1H, 2xs), 6.7(1H, s), 8.7(1H, br s)                                158    1.0(9H, s), 1.2(3H, t), 2.2(3H, s), 2.4(3H, s), 3.7(3H, s),                   4.0(2H, q), 4.8(1H, s), 6.1(1H, s), 8.9(1H, br s)                      159    1.0(9H, s), 3.9(6H, s), 4.8(1H, s), 7.5(2H, s), 11.8(1H, s),                  (in d.sup.6 -DMSO)                                                     160    1.0(9H, s), 2.5(3H, br d), 3.9(6H, s), 4.8(1H, s)                             7.5(1H, br q), 11.8(1H, br s), (in d.sup.6 -DMSO)                      161    1.0(9H, 2), 2.8(6H, s), 4.0(9H, s), 5.0(1H, s),                               8.4(1H, br s)                                                          162    1.0(9H, s), 1.1(3H, t), 2.8(3H, s), 3.3(2H, q), 3.9(6H, s),                   4.9(1H, s), 8.7(1H, br s)                                              163    1.1(9H, s), 2.5(3H, s), 2.7(3H, d), 4.0(3H, s), 5.0(1H, s),                   5.2(1H, br q)                                                          164    1.1(9H, s), 2.4(3H, s), 4.0(3H, s), 4.7(1H, s),                               7.5(2H, br s), 11.8(1H, br s) (in d.sup.6 -DMSO)                       165    1.0(9H, s), 1.2(3H, t), 2.4(3H, s), 3.9(6H, s), 4.0(2H, m),                   4.8(1H, s), 9.5(1H, br s)                                              166    40.4    40.4     5.0   5.5    18.8  18.1                               ______________________________________                                    

EXAMPLE 167

Herbicidal Activity

To evaluate their herbicidal activity, compounds according to theinvention were tested using as representative range of plants: maize,Zea Mays (Mz); rice, Oryza sativa (R); barnyard grass, Echinochloacrusgalli (BG); oat, Avena sativa (O); linseed, Linum usitatissimum (L);mustard, Sinapsis alba (M); sugar beet, Beta vulgaris (SB); and soyabean, Glycine max (S).

The tests fall into two categories, pre-emergence and post-emergence.The pre-emergence tests involved spraying a liquid formulation of thecompound onto the soil in which the seeds of the plant species mentionedabove had recently been sown. The post-emergence tests involved twotypes of tests, viz., soil drench and foliar spray tests. In the soildrench tests the soil in which the seedling plants of the above specieswere growing was drenched with a liquid formulation containing acompound of the invention, and in the foliar spray tests the seedlingplants were sprayed with such a formulation.

The soil used in the tests was a prepared horticultural loam.

The formulations used in the tests were prepared from solutions of thetest compounds in acetone containing 0.4% by weight of analkylphenol/ethylene oxide condensate available under the trademarkTRITON X-155. These acetone solutions were diluted with water and theresulting formulations applied at dosage levels corresponding to 5 kg or1 kg of active material per hectare in a volume equivalent to 600 litersper hectare in the soil spray and foliar spray test, and at a dosagelevel equivalent to 10 kilograms of active material per hectare in avolume equivalent to approximately 3,000 liters per hectare in the soildrench tests.

In the pre-emergence tests untreated sown soil and in the post-emergencetests untreated soil bearing seedling plants were used as controls.

The herbicidal effects of the test compounds were assessed visuallytwelve days after spraying the foliage and the soil, and thirteen daysafter drenching the soil and were recorded on a 0-9 scale. A rating 0indicates growth as untreated control, a rating 9 indicates death. Anincrease of 1 unit on the linear scale approximates to a 10% increase inthe level of effect.

The results of the tests are set out in Table IV below, in which thecompounds are identified by reference to the preceding Examples. Absenceof a numeral in the Table indicates a zero rating; an asterisk indicatesthat no result was obtained.

                                      TABLE IV                                    __________________________________________________________________________    Com-                                                                          pound of                                                                           Soil drench 10 kg/ha                                                                            Dosage                                                                            Foliar spray      Pre-emergence                    Ex. No.                                                                            Mz R BG O L M SB                                                                              S kg/ha                                                                             Mz R BG O L M SB                                                                              S Mz R BG O L M SB                                                                              S                __________________________________________________________________________     3   7  7 7  6 7 8 7 8 5   7  7 8  7 7 9 9 7 8  8 8  7 8 8 8 8                                       1   2  6 7  4 7 9 8 6 7         6                                                                             6                                                                             2                                                                             7 8 8 3                 4   5  8 9  8 8 9 9 7 5   8  8 8  8 8 9 8 8 8         9                                                                             9                                                                             8                                                                             9 8 8 6                                       1   5  5 8  7 8 8 8 8 3         6                                                                             8                                                                             4                                                                             8 8 8 4                 5   4  6 6  5 5 6 7 5 5      5 8  4 5 8 8 7 7         7                                                                             5                                                                             2 7 7 6                                       1      2 2  1   7 7 4 5         2 5 5 4                 6   6  6 6  4 7 8 8 6 5   6  7 9  7 8 8 9 8 8         8                                                                             6                                                                             6                                                                             7 8 7 4                                       1   2  5 8  3 7 8 8 7 2         2                                                                             1                                                                             2 7 5 1                 7                     5        4  2 2 8 7 5                                                         1               7 5                                     8   7  7 6  5 6 9 8 7 5   8  8 8  8 7 9 9 8 7         8                                                                             6                                                                             7                                                                             7 7 8 8                                       1   2  3 7  3 7 8 8 8 3         6                                                                             2                                                                             3 7 7 3                 9   4  6 6  4 5 7 7 4 5   3  3 7  3 5 9 8 4 6         7                                                                             7                                                                             6                                                                             7 8 8 4                                       1             3 8 8 2 2         5                                                                             2 7 8 3                10   8  7 7  8 8 9 7 7 5   6  7 7  7 8 8 8 7 8         8                                                                             8                                                                             8                                                                             8 8 8 7                                       1   4  5 6  6 7 7 7 6 5         7                                                                             6                                                                             5                                                                             3 8 7                  11   2  4 3    5 7 7 5 5   7  7 8  7 8 9 9 8 8         8                                                                             9                                                                             7                                                                             8 8 8 8                                       1   2  6 8  5 8 8 8 7           6                                                                             5                                                                             3                                                                             4 7 5                  12   4  6 6  4 5 8 8 5 5   7  8 8  5 8 9 9 8 8         8                                                                             8                                                                             6                                                                             8 8 8 8                                       1      6 8  2 7 8 8 7 2         4                                                                             5                                                                             3                                                                             6 8 8 2                13   8  6 8  7 8 9 9 * 5   9  8 9  7 8 9 9 8 9         9                                                                             9                                                                             8                                                                             8 8 8 8                                       1   7  7 9  5 8 9 8 7 6         6                                                                             7                                                                             4                                                                             7 8 8 6                14   8  7 8  7 6 9 9 7 5   7  7 8  7 7 9 9 8 8         9                                                                             9                                                                             7                                                                             7 8 9 7                                       1   4  6 7  6 3 8 8 6 5         7                                                                             6                                                                             5                                                                             5 8 8                  15   6  6 7  6 4 9 9   5   5  5 7  6 7 9 9 2 6         8                                                                             6                                                                             6                                                                             1 7 8                                         1   1  4 6  2 2 8 8   2         5                                                                             2 7 7                  16        4    4 6 3 2 5               8 6 7 3         2                                                                             2                                                                             2                                                                             4 7 7 4                                       1               7 6 2           2                                                                             2                                                                             2 6 6                  17   3  2 5  2 5 6   2 5   3    2    5 9 8 7 2         2 6 7 4                                       1               7 6 2             6 6                  18   6  3 2  1 4 7 4 3 5   4  4 7  3 6 9 8 6 5         7                                                                             7                                                                             3                                                                             6 7 8 6                                       1   4    6  2 4 8 6 5             7 7 2                19   6  7 *  3 2 7 7 1 5   6  6 7  2 3 7 8 6 6         8                                                                             7                                                                             3                                                                             2 7 7 3                                       1   1  6 6    2 7 7 6             7 6                  20   8  7 7  7 2 8 7 * 5   8  6 7  7 5 9 9 8 8         7                                                                             8                                                                             6                                                                             3 7 8 5                                       1   5  6 6  5 4 8 7 6 6         6                                                                             6                                                                             5 7 7 5                21   8  8 9  6 7 8 * 4 5   8  7 9  7 8 9 9 9 9         8                                                                             9                                                                             7                                                                             8 8 8 7                                       1   7  7 8  6 7 8 8 7 8         7                                                                             8                                                                             5                                                                             7 8 8 6                22   6  6 7  4 7 8 6 6 5   7  7 8  7 7 9 8 8 8         9                                                                             9                                                                             8                                                                             8 8 8 7                                       1   6  7 8  6 7 8 8 7 6         7                                                                             7                                                                             5                                                                             6 8 8 6                23        5      6 *   5   2    8    4 8 8 4 3         7 7 7 4                                       1        5      7 7 2             7 4 4                24   4  5 6      6 5   5   5  2 7    5 8 8 6 7         5                                                                             7                                                                             3 7 4 3                                       1   2    5      6 6 5 2         2 6                    25   8  7 8  7 7 8 7 6 5   8  7 9  8 7 9 8 7 8         9                                                                             9                                                                             7                                                                             8 7 8 6                                       1   5  7 8  7 7 8 8 5 6         6                                                                             7                                                                             4                                                                             6 7 7 4                26   7  8 8  7 7 8 8 7 5   8  7 8  7 7 9 8 8 8         9                                                                             9                                                                             7                                                                             7 7 8 7                                       1   7  7 8  7 7 8 7 6 6         8                                                                             8                                                                             7                                                                             6 7 7 6                27   8  8 8  7 6 7 8 7 5   8  7 9  7 8 9 9 8 9         9                                                                             9                                                                             7                                                                             7 7 8 9                                       1   8  7 8  6 8 9 8 7 9         8                                                                             8                                                                             5                                                                             6 7 7 8                28   8  5 6  5 6 7 5 5 5   6  4 8  5 7 9 8 8 6         7                                                                             8                                                                             3                                                                             6 7 6 5                                       1   5    7  5 7 8 7 6 2         2                                                                             4                                                                             1                                                                             4 7 5 2                29   8  8 9  7 7 8 8 8 5   8  7 8  4 7 8 8 7 9         9                                                                             9                                                                             7                                                                             7 7 8 9                                       1   7  5 8  4 7 8 7 7 8         8                                                                             9                                                                             5                                                                             5 7 8 4                30   6  7 6  5 7 7 7 4 5   5  7 8  6 6 8 8 7 7         8                                                                             7                                                                             7                                                                             7 7 7 4                                       1   2  6 7  6 6 7 7 4 4         4                                                                             2                                                                             4                                                                             5 5 6 2                31   8  8 8  7 7 9 9 7 5   7  7 9  7 7 8 8 8 8         9                                                                             9                                                                             8                                                                             7 7 8 7                                       1   6  7 8  7 7 7 7 7 7         8                                                                             8                                                                             7                                                                             6 7 7 6                32   6  8 7  4 7 7 7 6 5   7  8 8  7 7 8 9 7 8         9                                                                             9                                                                             8                                                                             8 7 8 8                                       1   6  7 7  6 7 7 7 2 6         8                                                                             7                                                                             2                                                                             7 7 7 5                33   7  7 7  6 7 7 8 5 5   6  8 8  7 7 8 8 6 8         9                                                                             8                                                                             7                                                                             8 7 8 7                                       1   5  8 8  6 7 7 7 3 6         8                                                                             6                                                                             2                                                                             7 7 8 4                34   5    6  1 2 7 2 2 5   4  2 7  3 6 7 7   7         6                                                                             7                                                                             4                                                                             6 7 7 6                                       1   2    3    5 7 6   2         2 6 5                  35   6  8 8  6 4 7 6 4 5   6  7 7  6 6 9 9 5 7         9                                                                             8                                                                             8                                                                             6 7 8 8                                       1   4  7 7  5 5 8 8 4 4         8                                                                             7                                                                             5 7 7 7                36   6  5 8  2 7 9 8 5 5   6  8 8  7 7 8 8 8 8         9                                                                             8                                                                             7                                                                             8 7 8 8                                       1   5  7 7  2 7 7 7 2 2         2                                                                             7                                                                             2                                                                             7 7 7 2                37   7  7 8  7 3 7 7 7 5   7  7 7  5 6 8 8 7 7         9                                                                             8                                                                             7                                                                             4 7 7 7                                       1   5  7 7  5 5 7 7 2 5         6                                                                             7                                                                             2 7 7 2                38   7  7 7  7 7 7 7 8 5   6  6 8  6 7 8 7 8 8         9                                                                             8                                                                             7                                                                             6 7 7 8                                       1   5  5 7  4 7 7 7 7 6         2                                                                             6,                                                                            4                                                                             6 7 7 8                39   7  7 8  7 7 7 6 5 5   7  3 8  3 7 7 7 4 8         8                                                                             8                                                                             3                                                                             4 7 7 6                                       1   2  1 7  1 6 7 6 2 5         2                                                                             5                                                                             1 6 6 5                40   5  6 6  7   7 8   5   6  6 7  4 6 8 9 6 7         9                                                                             8                                                                             7                                                                             6 7 7 8                                       1   3  2 6  2 3 7 8 2 5         7                                                                             7                                                                             5                                                                             4 7 7 6                41   7  8 7  7 6 7 7 8 5   7  8 8  7 7 8 9 7 8         9                                                                             9                                                                             8                                                                             8 7 7 8                                       1   6  7 7  7 7 7 9 6 7         9                                                                             7                                                                             7                                                                             7 7 7 6                42   6  8 7  7 7 7 7 6 5   6  7 7  7 7 8 7 7 8         9                                                                             8                                                                             7                                                                             8 7 8 8                                       1   4  2 4  5 7 7 7 6 7         7                                                                             7                                                                             6                                                                             7 7 7 6                43   7  7 7  7 7 7 7 7 5   8  8 8  7 7 8 9 7 8         9                                                                             8                                                                             7                                                                             8 7 8 9                                       1   7  7 7  6 7 8 8 6 7         7                                                                             7                                                                             6                                                                             7 7 7 8                44   4  2 6  2 3 8 2 6 5   4  3 7  2 7 8 7 7 4         7                                                                             7                                                                             4                                                                             6 7 7 6                                       1   2  1 5    6 7 6 4 2         5                                                                             2                                                                             3 7 7 2                45   5  7 7  5 5 7 7 6 5   6  7 8  4 7 8 7 7 7         8                                                                             8                                                                             7                                                                             7 7 7 9                                       1   4  2 7  2 4 7 7 5 5         6                                                                             7                                                                             4                                                                             2 7 7 6                46   6  7 7  7   9 7   5   7  7 7  7 6 8 8 6 8         8                                                                             8                                                                             7                                                                             6 7 7 6                                       1   2  6 7  6 2 7 7 5 7         7                                                                             6                                                                             4 7 7 5                47   5  7 6  2   7 6 6 5   4    6    5 8 8 5 7         7                                                                             7                                                                             7 7 7 8                                       1        2      7 7 4 4         5                                                                             2 6 7 7                48        4    3 7     5   4    7  2 7 8 8 5 5         6 7                                           1   2    3    6 7 7   2           6                    49   8  8 8  8 7 8 8 7 5   6  8 8  7 7 8 8 7 9         9                                                                             9                                                                             8                                                                             9 8 8 8                                       1   3  7 8  6 7 7 7 5 7         8                                                                             8                                                                             7                                                                             8 8 8 7                50   *  * *  * * * * * 5   7  7 8  6 7 8 8 7 8         8                                                                             9                                                                             8                                                                             8 8 8 7                                       1   4  3 8  4 7 7 8 5 8         6                                                                             8                                                                             6                                                                             6 8 8 5                51   8  8 8  7 6 8 8 7 5   8  8 8  7 7 8 8 7 9         9                                                                             9                                                                             8                                                                             7 8 8 8                                       1   6  8 8  6 7 7 7 5 5         9                                                                             7                                                                             5                                                                             4 8 8 3                52   7  8 7  4 2 8 8 5 5   5  6 8  2 5 8 8 5 8         8                                                                             9                                                                             6                                                                             7 7 8 8                                       1   3  5 8    3 6 7 2 3         3                                                                             6                                                                             5                                                                             2 7 8 5                53   8  7 8  7   8 8 6 5   6  6 8  5 3 8 8 5 8         8                                                                             9                                                                             8                                                                             5 8 8 6                                       1   4  2 8  2   7 7 2 6         7                                                                             8                                                                             7                                                                             2 8 8 5                54   8  8 8  8 6 8 8 6 5   7  8 8  8 7 8 8 6 9         9                                                                             9                                                                             8                                                                             8 8 8 8                                       1   4  7 8  7 7 7 7 4 6         9                                                                             7                                                                             7                                                                             5 8 8 6                55   8  7 7  7   8 8   5   5  4 8    2 8 8 5 7         8                                                                             9                                                                             7 8 8 5                                       1   1  2 7      7 7 2 3         7                                                                             7                                                                             4 8 7                  56   5    7  6 5 7 6 5 5   7  2 8  5 7 8 8 5 8         6                                                                             8                                                                             7                                                                             7 7 7 7                                       1   5  1 7  4 7 7 7 2 7         2                                                                             7                                                                             2                                                                             5 7 7 5                57   4    7    6 7 6   5   6    7  4 7 7 7 3 7         7                                                                             7                                                                             4                                                                             7 7 7 4                                       1   4    5  2 6 7 7 2 5         2                                                                             6                                                                             2                                                                             6 7 7                  58   6  7 7  6 5 7 6 7 5   6  7 7  6 6 7 7 6 8         9                                                                             8                                                                             7                                                                             7 7 7 7                                       1   4  6 7  5 6 6 7 2 6         8                                                                             7                                                                             6                                                                             2 7 7 5                59   6  7 7  6 4 7 4 5 5   6  7 7  5 7 7 7 4 8         9                                                                             8                                                                             7                                                                             7 7 7 7                                       1   2  6 7  2 6 7 7 2 4         7                                                                             7                                                                             6 6 7 2                60   7  6 7  7   7 7   5   5  4 7  4 7 8 8 4 7         7                                                                             7                                                                             7                                                                             6 7 7 4                                       1   2  2 7  2   7 7 2 6         5                                                                             5                                                                             2 7 7 2                61   7  8 8  6 7 8 8 7 5   6  7 8  6 7 8 8 9 8         9                                                                             9                                                                             7                                                                             8 7 7 8                                       1   4  5 8  2 7 7 7 8 7         7                                                                             7                                                                             4                                                                             7 7 7 8                62   7  8 8  7 7 7 7 8 5   7  7 7  7 7 7 8 8 9         9                                                                             9                                                                             8                                                                             8 7 7 8                                       1   6  7 7  6 7 7 7 7 8         9                                                                             8                                                                             6                                                                             7 7 7 8                63   7  8 8  7 5 7 7 6 5   8  8 7  5 7 8 8 7 8         9                                                                             8                                                                             7                                                                             7 7 7 8                                       1   7  7 7  2 7 7 7 6 6         9                                                                             7                                                                             7                                                                             7 7 7 6                64   7  6 7  7   7 7   5   5  4 7  4 7 8 8 4 7         7                                                                             7                                                                             7                                                                             6 7 7 4                                       1   2  2 7  2   7 7 2 6         5                                                                             5                                                                             2 7 7 2                65   7  8 7  7 7 7 6 7 5   8  8 8  7 7 8 8 8 8         9                                                                             8                                                                             8                                                                             8 7 7 8                                       1   5  8 7  6 7 7 7 8 6         9                                                                             7                                                                             7                                                                             6 7 6                  66   7  8 8  7 7 7 7 7 5   7  8 8  7 7 8 8 8 8         9                                                                             9                                                                             8                                                                             8 8 8 9                                       1   5  8 7  6 7 7 7 7 7         8                                                                             8                                                                             2                                                                             7 7 7 2                67   7  6 7  7 7 7 7 7 5   8  7 9  7 7 8 8 8 9         9                                                                             9                                                                             7                                                                             8 7 8 8                                       1   7  2 8  5 7 7 7 7 8         4                                                                             8                                                                             2                                                                             7 7 7 2                68   6  6 5  6 6 7 6 5 5   7  7 8  6 7 8 9 7 8         8                                                                             7                                                                             7                                                                             7 7 7 7                                       1   5    7  4 7 8 7 5 7         6                                                                             6                                                                             5 7 6 4                69   7  7 7  6 5 7 7 6 5   6  7 8  6 7 8 8 8 7         9                                                                             8                                                                             6                                                                             7 7 7 8                                       1   4  2 7  4 7 8 7 6 6         6                                                                             6                                                                             5 7 7 2                70   7  8 7  6 6 7 8 6 5   7  7 8  7 7 7 8 7 8         9                                                                             8                                                                             7                                                                             7 7 8 8                                       1   5  7 7  7 7 7 7 6 6         8                                                                             7                                                                             5                                                                             2 7 7 7                71   5  8 7  2 2 7 4 2 5   3  7 8  6 7 7 7 5 5         9                                                                             8                                                                             4                                                                             6 7 8 4                                       1      2 7  5 6 7 7 2 2         6                                                                             6                                                                             2                                                                             2 7 7 2                72   7  8 7  7 6 7 7 4 5   7  8 8  7 7 7 8 6 8         9                                                                             9                                                                             6                                                                             7 7 8 7                                       1   4  8 8  5 6 7 7 6 7         9                                                                             8                                                                             5                                                                             6 7 7 7                73   6  7 7  4 7 7 7 5 5   5  7 7  4 7 7 7 6 6         9                                                                             4                                                                             5                                                                             8 7 4 5                                       1   *  * *  * * * * * *         *                                                                             *                                                                             *                                                                             * * * *                74   8  4 8  7 4 7 7 5 5   8  5 8  4 7 7 8 7 8         8                                                                             8                                                                             8                                                                             7 7 8 7                                       1   6  4 8  2 6 7 7 6 6         7                                                                             7                                                                             6                                                                             4 7 7 6                75   7  7 8  7 4 7 7 4 5   8  6 8  7 7 8 8 7 8         9                                                                             8                                                                             8                                                                             4 7 8 5                                       1   6  5 8  6 6 7 7 5 6         8                                                                             7                                                                             6 7 8 4                76   5  2 7  6 4 7 8 5 5   6    8  1 6 8 8 4 7         7                                                                             8                                                                             4                                                                             2 7 7 7                                       1   2    7    4 7 7 2 5         5                                                                             7                                                                             2 7 7 4                77   5  2 7  2 3 6 7 4 5   6  1 8  4 4 8 8 4 6         7                                                                             7                                                                             2                                                                             2 7 8 6                                       1   2    7    2 7 7 2 5         4                                                                             6 7 7 2                78   7  6 7  6   7 7 6 5   5  6 7  5 6 7 7 2 7         8                                                                             7                                                                             5 7 8 6                                       1   2  6 6  2 2 7 7   6         7                                                                             7                                                                             2 7 8 2                79   7  6 7  6 7 8 7 7 5   6  4 7  4 7 9 9 6 8         9                                                                             8                                                                             7                                                                             7 8 8 8                                       1   4  2 7  2 7 8 9 5 7         8                                                                             6                                                                             4                                                                             2 7 7 8                80   7  6 7  4 5 7 7 7 5   7  6 7  6 7 7 8 6 7         9                                                                             8                                                                             6                                                                             4 7 8 8                                       1   6  5 7  5 6 7 7 4 5         9                                                                             7                                                                             2 7 8 8                81   6  5 7  2   7 7 6 5   6  4 8  4 5 7 8 6 7         7                                                                             8                                                                             6                                                                             5 7 7 8                                       1   2  4 7  2 2 7 7 2 5         2                                                                             7 7 7 6                82   7  6 7  6 5 7 7 6 5   6  5 7  4 7 9 9 5 7         9                                                                             7                                                                             4 7 8 8                                       1   4  5 6  2 6 8 8 2 5         6                                                                             4                                                                             2 7 8 7                83   7  5 6  7   9 7 6 5   7  4 7  4 5 9 8 6 8         9                                                                             9                                                                             7 7 8 7                                       1   5  2 6  2   8 8 5 7         8                                                                             7                                                                             6 7 7 6                84   8  6 8  8 7 6 6 7 5   8  6 8  8 7 8 8 8 8         9                                                                             8                                                                             8                                                                             8 8 8 6                                       1   7  6 8  7 6 8 8 7 7         9                                                                             8                                                                             7                                                                             6 8 7 2                85   8  6 8  8 7 8 8 6 5   7  6 8  7 7 8 8 8 8         9                                                                             8                                                                             8                                                                             8 8 8 7                                       1   6  6 7  5 6 7 7 8 7         7                                                                             8                                                                             6                                                                             6 7 7 5                86   7  2 7  4 6 7 6 6 5   5  5 7  2 6 8 7 7 7         8                                                                             8                                                                             7                                                                             5 8 7 1                                       1   2  2 6    5 7 6 6 2         1                                                                             2                                                                             1                                                                             1 7 5 1                87   3  4 2  3   7 6   5   4  3 7  4   7 8 4 7         7                                                                             8                                                                             6                                                                             4 7 7                                         1   2    5  2   7 7 2 5         6                                                                             6                                                                             5                                                                             2 7 7                  88   6  7 6  5 2 7 6 2 5   6  5 7  6 4 7 7 4 7         9                                                                             8                                                                             7                                                                             6 7 8 6                                       1   2  5 7  2 2 7 7 2 6         8                                                                             7                                                                             7                                                                             2 7 8 5                89   6  4 6  7 2 7 6 4 5   6  5 8  7   8 7 5 8         8                                                                             8                                                                             8                                                                             6 7 8 7                                       1   2  2 7  2   7 6 4 7         7                                                                             7                                                                             7 7 7 6                90   3  2 7  6   7 6   5   4  6 7  4 2 8 8 4 7         8                                                                             8                                                                             8                                                                             4 7 7                                         1   2  2 5  2   7 6 2 6         7                                                                             7                                                                             8 7 6                  91   2    4      7 2 2 5   7  7 7  7 7 8 8 7 7         9                                                                             7                                                                             6                                                                             8 7 7 8                                       1   4  6 6  5 6 7 8 7 6         6                                                                             5                                                                             2                                                                             6 7 7 8                92   3  4 6  3 4 7 7 5 5   4  3 7  4 7 8 7 6 5         6                                                                             6                                                                             5                                                                             6 7 7 4                                       1   2  2 6  2 6 7 7 5 1         2                                                                             2                                                                             2                                                                             2 6 6 2                93   7  6 5  4 7 6 5 6 5   2  4 7  3 7 8 8 6 7         6                                                                             5                                                                             6                                                                             7 7 7 4                                       1      2 5    6 7 7 4 4         2                                                                             2                                                                             6 6 6 2                94   5  6 4  1 1 7 7 5 5   4  7 8  7 7 8 8 6 7         8                                                                             8                                                                             4                                                                             5 7 7 4                                       1   2  6 7  2 6 7 8 5 4         6                                                                             6                                                                             2                                                                             2 7 6 3                95   6  4 4  4 7 7 7 4 5   5  4 7  4 7 8 8 6 4         6                                                                             7                                                                             6                                                                             6 7 7 4                                       1   1  2 6    7 8 7 4 2         5                                                                             2                                                                             5                                                                             2 6 7                  96   3  2 4  2 3 6 6 4 5   7  5 7  7 7 7 8 6 7         6                                                                             4                                                                             4                                                                             5 7 7 5                                       1   2  2 4  2 6 7 7 5 2         2                                                                             2                                                                             2 7 7 4                97   7  7 6  5 6 7 7 5 5   7  6 7  7 7 8 9 5 9         9                                                                             8                                                                             8                                                                             7 7 7 5                                       1   5  5 6  5 6 7 8 4 7         8                                                                             6                                                                             6                                                                             6 7 6 2                98   7  8 7  6 6 7 8 6 5   7  7 8  7 7 8 9 7 8         9                                                                             8                                                                             8                                                                             7 7 8 8                                       1   6  7 8  5 6 7 8 6 7         8                                                                             7                                                                             5                                                                             6 7 7 6                99   *  * *  * * * * * 5   6  4 7  5 2 8 9 6 7         8                                                                             8                                                                             6 7 8 7                                       1   4  2 6  2   8 8 6 5         7                                                                             7                                                                             2 7 7 2                100  7  6 7  7 6 6 7 5 5   7  6 8  6 7 8 8 5 8         9                                                                             8                                                                             7                                                                             7 7 7 8                                       1   6  6 7  4 7 7 7 4 6         9                                                                             7                                                                             6                                                                             6 7 7 7                101  7  6 7  6   7 6 5 5   7  5 8  4 1 8 8 7 8         8                                                                             8                                                                             8 7 7 7                                       1   4  4 7  2   7 7 5 6         7                                                                             6                                                                             6 7 7 2                102  7  7 6  6   8 6 5 5   7  6 7  4 3 8 8 6 7         9                                                                             9                                                                             6                                                                             4 7 7 5                                       1   2  2 7  2 1 7 7 5 6         2                                                                             6                                                                             5 6 5                  103  7  2 6  7   9 7 3 5   4  3 7  3   9 8 5 6         2                                                                             8                                                                             7                                                                             5 7 7 2                                       1   2    5      8 6 4 2         6                                                                             6                                                                             2 5 5                  104  6  7 6  6 2 7 7 2 5   6  7 7  5 5 7 7 6 5         6                                                                             6                                                                             7                                                                             6 8 7 2                                       1   2  6 7  2 5 7 6 4 2         5                                                                             5                                                                             7                                                                             2 7 7                  105  7  7 7  7 5 8 7 7 5   8  7 8  8 6 8 8 8 8         9                                                                             8                                                                             7                                                                             8 8 8 5                                       1   5  7 8  7 2 7 7 6 7         8                                                                             5                                                                             6                                                                             5 8 7 2                106  6  7 7  4 7 8 7 6 5   6  7 7  4 6 8 8 4 8         9                                                                             7                                                                             7                                                                             8 8 8 8                                       1   5  6 5  2 6 7 7 2 6         7                                                                             6                                                                             6                                                                             7 8 7 6                107  7  4 7  2 4 7 6 4 5   3  6 6  4 6 8 8 7 4         7                                                                             8                                                                             2                                                                             2 7 8 2                                       1   1  2 6    5 8 7 2 2         2                                                                             4 6 8                  108  3  7 6  2 2 8 7 2 5   4  7 7  2 4 9 8 4 7         7                                                                             6                                                                             4 7 8 2                                       1   2  7 7      8 7   4         6                                                                             6 5 7                  109  7  7 6  7 4 8 7 6 5   7  6 8  7 6 9 9 8 8         9                                                                             8                                                                             8                                                                             7 8 8 8                                       1   6  5 7  7 5 8 8 7 7         9                                                                             7                                                                             6                                                                             6 7 7 4                110  8  8 4  3 8 9 9 8 5   6  7 7  7 8 9 9 7 4         *                                                                             7                                                                             4                                                                             8 8 8 8                                       1   1  6 7  5 8 9 8 6           2                                                                             3                                                                             6 8 8 6                111  7  8 8  7 7 8 8 7 5   7  8 8  6 8 9 9 9 7         9                                                                             8                                                                             7                                                                             7 8 8 8                                       1   5  8 8  5 7 8 8 8 2         8                                                                             6                                                                             6                                                                             2 8 7 2                112  7  8 6  4 6 7 4 5 5   7  4 7  7 7 8 8 4 7         8                                                                             6                                                                             4                                                                             3 5 6 4                                       1   6  2 7  5 7 8 7 2 2         7                                                                             2                                                                             2 2 5 2                113  7  6 4  3 2 7 5 4 5   7  6 8  5 7 8 8 6 8         8                                                                             6                                                                             4                                                                             2 7 8 2                                       1   4  5 7  4 6 8 8 5 2         7                                                                             4                                                                             2 6 7                  114                    5             4 6 4 5                                                         1             2 2 2 4                                  115  6  8 6  7   8 8 6 5   4  7 7  2 4 9 8 6 4         8                                                                             8                                                                             4 8 8 4                                       1   2  6 7    2 8 8 5 2         7                                                                             8                                                                             2 8 8 2                116  7  8 6  5   8 6 4 5   7  6 7  4 4 8 8 4 6         8                                                                             7                                                                             6                                                                             4 7 8 5                                       1   2  5 7  2 2 7 7 2 5         6                                                                             6                                                                             2                                                                             2 6 7 4                117  7  6 6  4   6 6 5 5   3  4 7  4   8 8 6 6         7                                                                             6                                                                             2 6 8 6                                       1   1  2 6  2   7 7 4 5         2                                                                             5 5 7 5                118  7  6 7  6 5 7 6 7 5   7  7 8  6 7 7 8 6 7         8                                                                             6                                                                             4                                                                             6 8 8 5                                       1   4  7 8  2 2 6 8 5 2         7                                                                             5                                                                             2                                                                             2 7 7 4                119  7  8 7  7 7 8 8 8 5   8  8 8  7 8 8 8 8 8         9                                                                             8                                                                             4                                                                             8 8 8 7                                       1   7  8 8  6 7 8 7 7 7         7                                                                             2                                                                             2                                                                             2 8 7 4                120            2 8 7   5                                                                             1                                                      121              8 4   5               7 7 2             7                                           1               6 5               7                    122  7  8 7  7 4 8 7 6 5   7  8 8  7 7 8 8 8 4         8                                                                             7                                                                             6                                                                             4 8 8 2                                       1   5  8 8  6 5 8 8 7 2         8                                                                             4                                                                             5 8 7                  123  7  8 8  7 7 8 8 7 5   6  7 8  7 7 8 9 7 8         9                                                                             7                                                                             6                                                                             8 8 8 6                                       1   5  7 8  6 6 7 8 6 4         8                                                                             6                                                                             5                                                                             2 8 7 5                124  4  7 7  4   7 6 7 5   2  6 6      8 8 2 3         7                                                                             5                                                                             2 8 8 2                                       1      5 2      7 7             6                                                                             4 7 6                  125  7  6 6  2 7 7 9 7 5   4  7 8  4 8 8 9 7 6         4                                                                             7                                                                             2                                                                             7 8 8 8                                       1      4 7  2 7 8 8 6           2                                                                             2                                                                             2 7 7 7                126                    5               4 2                                                           1               2                                      127  6  5 7  4   7 8 6 5   2  1 8  1 2 8 8 4 2         1                                                                             4 8 8 4                                       1        2      8 8 2           2 7 6 2                128  5  7 7  6   8 8 2 5   7  5 8  3   8 8 2 6         6                                                                             8                                                                             4 8 7 2                                       1   2  2 2      8 8   5         4                                                                             7                                                                             2 8 6                  129  7  5 7  6 5 7 6 5 5   7  7 8  5 8 8 9 8 7         7                                                                             7                                                                             4                                                                             6 7 8 4                                       1   2  6 7  4 8 8 8 6 2         2                                                                             2                                                                             2 6 7 2                130  8  8 7  6 8 8 8 8 5   8  8 8  8 8 9 9 8 8         9                                                                             7                                                                             6                                                                             8 8 8 6                                       1   5  8 8  5 8 8 9 8 4         7                                                                             4                                                                             5                                                                             4 8 6 5                131       4  2   8 8 5 5        5  2 7 8 8 7 2         4                                                                             3                                                                             2 7 7 5                                       1        2    2 8 7 6           2 7 5 4                132  6  7 6  7 7 7 8 5 5   5  7 8  2 6 8 8 6 4         8                                                                             7                                                                             4                                                                             7 8 8 5                                       1   *  * *  * * * * * *         *                                                                             *                                                                             *                                                                             * * * *                139  8  6 8  6 6 7 5 8 5   8  6 8  7 7 8 8 8 7         9                                                                             8                                                                             7                                                                             8 7 8 8                                       1   7  4 7  6 6 8 6 7 5         8                                                                             7                                                                             5                                                                             5 7 8 7                140  3  7 6  7 7 8 4 7 5   7  7 8  6 8 8 8 7 5         9                                                                             5                                                                             6                                                                             8 8 8 8                                       1   5  4 8  5 8 8 8 6 3         4                                                                             3                                                                             2                                                                             7 8 8 8                141  7  8 7  2 8 8 8 8 5   6  7 7  4 8 9 9 9 6         7                                                                             8                                                                             8 8 8 9                                       1   5  5 7  2 8 8 8 8 5         6                                                                             6                                                                             6 8 8 9                142  8  8 7  6 7 8 8 8 5   8  8 8  6 8 8 8 8 5         8                                                                             8                                                                             7                                                                             8 8 8 8                                       1   6  8 8  5 7 8 8 8           7                                                                             7                                                                             6                                                                             8 8 8 7                143  8  8 6  4 7 8 7 7 5   8  8 8  2 8 9 8 8 7         8                                                                             3                                                                             2                                                                             7 8 8 7                                       1   8  7 8  2 8 8 7 8 2         4                                                                             2                                                                             1                                                                             5 8 7 5                144  7  7 6  5 2 8 4 8 5   7  8 8  6 7 8 8 7 7         8                                                                             7                                                                             4                                                                             5 8 8 8                                       1   4  8 8  5 7 8 8 7 6         7                                                                             6                                                                             2                                                                             4 8 8 8                145  6  5 4  6 5 7 4 6 5   6  7 8  5 7 8 8 5 4         4                                                                             4                                                                             2                                                                             3 8 8 6                                       1   5  7 7  4 7 8 8 4 4         2                                                                             2 7 8 5                146  7  7 8  6 8 8 9 7 5   7  7 8  4 8 9 8 7 8         8                                                                             8                                                                             4                                                                             8 8 8 7                                       1   6  5 8  1 7 8 7 7 6         7                                                                             6                                                                             2                                                                             6 8 8 7                147  7  7 8  6 8 8 8 7 5   7  7 8  2 8 8 8 8 8         9                                                                             8                                                                             7                                                                             8 8 8 8                                       1   4  6 7  2 7 7 8 7 4         8                                                                             6                                                                             5                                                                             6 8 7 7                148  8  8 7  7 8 8 8 7 5   8  7 8  6 8 9 9 8 8         9                                                                             8                                                                             7                                                                             8 8 8 8                                       1   6  6 8  2 8 8 8 7 6         8                                                                             8                                                                             5                                                                             7 8 8 7                149  8  7 8  7 8 8 8 7 5   7  7 9  8 8 9 9 8 7         9                                                                             8                                                                             6                                                                             6 7 7 5                                       1   7  7 8  7 8 8 8 7 7         8                                                                             7                                                                             6                                                                             6 7 7 4                150  6  7 7  6 8 8 8 7 5   6  5 9  7 8 8 8 8 8         8                                                                             7                                                                             7                                                                             6 7 7 7                                       1   4  2 7  6 8 8 8 7 7         7                                                                             6                                                                             7                                                                             5 7 7 7                151  7  6 7  6 7 8 8 7 5   4  6 8  7 8 8 8 7 8         7                                                                             6                                                                             2                                                                             8 8 8 8                                       1   2  2 7  5 7 8 8 7 5         2                                                                             5                                                                             7 8 8 7                152  7  6 7  5 6 8 7 6 5   7  7 9  7 7 8 8 8 7         8                                                                             7                                                                             6                                                                             5 6 7 4                                       1   6  6 8  6 7 7 8 6 5         7                                                                             6                                                                             6                                                                             4 5 7 2                153  7  7 6  7 7 8 8 6 5   7  7 8  6 8 8 9 8 7         5                                                                             7                                                                             5                                                                             4 6 5 2                                       1   5  7 7  5 8 7 7 7 6         4                                                                             6                                                                             4 5 2                  159  7  7 6  5 4 7 4 6 5   8  8 9  8 8 8 8 8 8         9                                                                             7                                                                             4                                                                             7 8 8 8                                       1   6  8 8  7 7 8 8 7 2         7                                                                             5                                                                             2                                                                             2 8 7 7                160  8  8 8  7 8 8 9 7 5   7  7 8  7 8 8 8 8 9         9                                                                             9                                                                             8                                                                             8 8 8 8                                       1   7  7 8  7 8 7 8 7 8         8                                                                             8                                                                             4                                                                             7 8 8 8                161  7  7 8  6 8 8 9 7 5   7  7 8  6 8 8 9 8 8         8                                                                             9                                                                             4                                                                             7 8 8 9                                       1   6  6 7  5 8 8 8 7 7         6                                                                             8                                                                             2                                                                             6 8 8 7                __________________________________________________________________________

What is claimed:
 1. A compound of the formula ##STR63## wherein A is CR⁷;R¹, R², and R⁷ are selected from the group consisting of hydrogen,halogen, formyl, cyano, carboxy, azido, alkyl, alkenyl, alkynyl,cycloalkyls, alkoxy, alkenylxoy, aryloxy, alkylthio, alkenylthio,alkynylthio, arylthio, alkylcarbonyl, alkoxy carbonyl, amino, aminoxy,and dialkyliminoxy groups; R³ is selected from the group consisting ofhydrogen, alkyl, alkenyl, alkynyl, cycloalkyls, aralkyl, and arylgroups; R⁴ is selected from the group consisting of hydrogen, alkyl,alkenyl, alkynyl, and acyl groups of the formula COR⁸ wherein R⁸ isselected from the group consisting of alkyl, aralkyl, and aryl groups;R⁵ and R⁶ are selected from the group consisting of hydrogen, alkyl,alkenyl, alkynyl, alkoxy, aryl, aralkyl, amino, cycloalkyls,heterocyclics, a group of the formula --SO₂ R⁸ wherein R⁸ is a member ofthe group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkoxy,aralkyl, amino, cycloalkyls, and heterocyclic groups; a group of theformula ##STR64## wherein R¹¹ is an alkylthio group, and R⁵ and R⁶ maybe taken together with the atom to which they are attached to form agroup of the formula ##STR65## wherein R⁹ and R⁰ are selected from thegroup consisting of alkyl, alkoxy, aryl, aralkyl, dialkylamine, and R⁹and R¹⁰ may be taken together with the atom to which they are attachedto form an aryl or heterocyclic group; or an agronomically acceptablesalt thereof; further wherein said alkyls of said compound are betweenC₁ and C₁₂, said alkenyls are between C₂ and C₁₂, said alkynyls arebetween C₂ and C₁₂, said cycloalkyls have between 3 and 8 ring members,said heterocyclic groups have between 5 and 6 ring members and aresingle ring systems, said heterocyclic groups further having one tothree hetero atoms therein selected from the group consisting of oxygen,nitrogen, and sulphur, provided that one hetero atom is nitrogen and atmost one oxygen or one sulfur; and said aryl groups are selected fromthe group consisting of single ring systems and fused ring systems, saidaryl groups further having between 6 and 10 ring members.
 2. Thecompound of claim 1, in which A represents CH.
 3. The compound of claim1, in which R¹ represents a C₁₋₄ alkyl, C₁₋₄ alkoxy, or C₁₋₄ haloalkylgroup.
 4. The compound of claim 3, in which R² represents a C₁₋₄ alkyl,C₁₋₄ alkoxy group or a halogen atom.
 5. The compound of claim 4, inwhich R³ represents a C₁₋₆ alkyl or a phenyl group.
 6. The compound ofclaim 5, in which R⁴ represents a hydrogen atom.
 7. A compound of claim6, in which R¹ is methyl, methoxy, or trifluoromethyl; R² is methyl,methoxy or chlorine; R³ is methyl, ethyl, n-propyl, i-propyl, n-butyl,i-butyl, s-butyl, t-butyl or phenyl; R⁴ is hydrogen; R⁵ is hydrogen,methyl or ethyl; R⁶ is hydrogen, methyl, ethyl, n-propyl, i-propyl,n-butyl, methoxy, chloroethyl, methoxycarbonylmethyl, mono- ordi-methoxyethyl, allyl, propynyl, cyclopropyl, cyclobutyl, pyridyl,dimethylpyrimidinyl, (dichlorocyclopropyl)methyl, phenyl, chlorophenyl,or benzyl, or a group ##STR66## or R⁵ and R⁶ together are ##STR67##together are --(CH₂)₂ O(CH₂)₂ --, --(CH₂)₂ N(CH₃)(CH₂)₂ -- or --(CH₂)₄--.
 8. The compound of claim 6 wherein R⁵ and R⁶ are selected from thegroup consisting of hydrogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₆ alkoxy,C₂₋₆ alkenyl, C₂₋₆ alkynyl, mono(C₁∝4 alkoxy)C₁₋₄ alkyl, di(C₁₋₄alkoxy)C₁₋₄ alkyl, (C₁₋₄ alkoxy)carbonyl (C₁₋₄ alkyl), C₃₋₈ cycloalkyl,benzyl, phenyl, pyridyl, pyrimidinyl, (C₃₋₈ cycloalkyl) C₁₋₄ alkyl, R⁵and R⁶ may be taken together with the atom to which they are attached toform a group having the formula ##STR68## wherein R¹¹ is C₁₋₄ alkylthio,R⁵ and R⁶ may be taken together with the atom to which they are attachedto form a group having the formula ##STR69## wherein R⁹ and R¹⁰ areselected from the group consisting of C₁₋₄ alkyl, C₁₋₄ alkoxy, di(C₁₋₄alkyl)amino, and R⁹ and R¹⁰ may be taken together with the atom to whichthey are attached to form a 5 membered ring having 2 to 3 hetero atomsselected from the group consisting of nitrogen and sulphur, providedthat one hetero atom is nitrogen and at most one sulfur, and whereinsaid ring is optionally substituted with C₁₋₄ alkyl.
 9. The compounds ofclaim 1 wherein said salts are selected from the group consisting ofagronomically acceptable salts with inorganic cations derived fromalkali metals, alkaline earth metals and transition metals, and saltswith organic cations.
 10. The compounds of claim 9 wherein said cationsare selected from the group consisting of sodium, potassium, calcium,magnesium, copper, alkylammonium and alkylsulfonium.
 11. The compoundsof claim 1 wherein said heterocyclic groups are selected from the groupconsisting of morpholino, piperazino, piperidino, pyrrolidino, pyridyl,pyrimidinyl, triazinyl, thiazolo, and thiadiazolo.
 12. A herbicidalcomposition comprising a compound of claim 1 combined with a member ofthe group consisting of carriers, surface-active agents, and mixtures ofcarriers and surface-active agents.
 13. A method of combatting undesiredplant growth at a locus, which comprises treating the locus with amember of the group consisting of the compound of claim 1, a combinationof the compound of claim 1 together with a carrier, a combination of thecompound of claim 1 together with a surface-active agent, and a mixtureof the compound of claim 1, surface-active agent, and carrier.